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Wealth of Wisdom

The Top 50 Questions Wealthy Families Ask

TOM McCULLOUGH | KEITH WHITAKER

Wealth of Wisdom Podcast

The Wealth of Wisdom podcast is meant to be an audio companion to the Wealth of Wisdom book. Each episode involves Tom or Keith interviewing one of the over 50 top global thinkers on family wealth that have contributed essays to the book. The interviews are intended to be conversations where the contributors will get a chance to talk about themselves, their work, and the ideas in their specific chapter in the book. We think there is real value in these interviews and we hope that everyone enjoys them.

EPISODE 31: Christian Stewart – What Are Practical Tools for Building Healthy Families?

What are tools to build healthy families? That’s the question that Keith Whitaker discusses with Christian Stewart in this podcast. Christian is a non-practicing solicitor in Hong Kong who consults with global families around family governance. Among other things, Christian describes exercises he uses with families around managing difficult conversations and expressing gratitude. He also talks about how advisors can develop a comfort level in deploying these tools with their families.

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EPISODE 30: Bob Maynard – Does Investing Have to Be Complicated?

In world where it is pretty much assumed you need a specialized and complex strategy to be a sophisticated investor, Robert Maynard argues that a simple, transparent and focused approach is a viable and successful alternative. He runs the $17 billion Public Employee Retirement fund for the state of Idaho and practices what he preaches. In this interview, Bob talks about the three ways to make money, the importance of understanding your goals, and the role of active management, among many other fascinating topics.

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EPISODE 29: Hartley Goldstone – How Do You Choose a Good Trustee?

In common law countries, a very large proportion of wealth will be held in trusts by the third generation. As such, finding and retaining good trustees will be increasingly important. Yet, somehow, family trusts often preserve a family’s financial assets, yet fail to preserve either family or trust. Hartley Goldstone, a trained lawyer and an experienced consultant to trusts and trustees, talks about how families can source great trustees and how trustees can ensure they fulfill their important responsibilities. He also shares the results of his substantial research and interviews with beneficiaries and trustees on what works most effectively and does the most good.

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EPISODE 28: John Davis – Why Is Family Unity So Important and How Can You Achieve It?

John Davis is a household name in the world of families and business. He is one of the creators of the three circle model, which has been a helpful tool for understanding how families, managers and owners interact in family enterprises for over 40 years. In this episode, John talks about how he found his way into this work, the history of the three circle model, why family unity is important and how it can be built, and the future of enterprising families.

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EPISODE 27: Charley Ellis – Is Active Management Still Worthwhile? Part 2 of 2

In this interview, renowned investor Charley Ellis pulls no punches. Active managers, he says, cannot beat the market on a consistent basis. Fifty years ago, Charley argues, institutions did less than 10% of total NYSE trading, and individuals did more than 90%, and beating the market was probable for well-informed professionals. Today, full-time professionals who are constantly comparison-shopping inside the market for any competitive advantage are executing more than 98% of trades in listed stocks, and nearly 100% of derivative transactions, which makes it almost impossible for the average manager or investor to outperform. A fascinating conversation about investment performance, fees, and the future of active management for private investors.

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EPISODE 26: Randolph Cohen – Is Active Management Still Worthwhile? Part 1 of 2

Even as passive investing continues to rise in popularity, many families struggle with the choice of active versus passive. In this podcast Harvard Business School professor Randy Cohen, a close researcher of investment returns, argues that there’s no going back to the days when famous managers could ‘beat’ efficient public markets. However, Cohen does identify four strategies that–with patience and the right advice–families should consider in order to achieve outsized returns with a significant part of their portfolios.

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EPISODE 25: Jim Garland – What Is the Most Useful Definition of Risk for Family Investors?

Risk is a commonly misunderstood concept – even more so for private clients, who have to operate in world that is increasingly tilted toward institutions and professional investors. In this interview, long-time investor Jim Garland, who shepherded the Jeffrey family portfolio for many years, provides his guidance on how families should think about investing and how they can manage risk. The way Jim thinks, risk means the possibility of not having available the money you need at the time when you need it. And you definitely want to hear his analogy about ‘Chicken farmers’ and ‘Egg farmers’.

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EPISODE 24: Ellen Perry – What Does Passing on Values to the Next Generation Really Look Like?

All parents want their children to learn good values. But what do we mean by values? And how are they learnt? These are just a couple of the questions that Ellen Perry takes on in her chapter and this podcast interview with Keith Whitaker. Ellen also discusses what families can do when there are real disagreements over values or the choices that those values lead to, as well as specific activities that parents and grandparents can use to prompt productive conversations among their family members about the values they hold dear.

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EPISODE 23: Dennis Jaffe – How Can You Engage Your Children in the Management of Your Family Wealth or Business?

There are strong forces against family business continuity. So every enterprise must find ways to engage the rising generation. In this interview with Tom McCullough, Dennis Jaffe talks about how business families can increase the critical elements of connection, transparency, capability, and commitment. He also highlights some of the best practices around designing and holding effective family meetings, which can help to sustain these family building blocks.

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EPISODE 22: Josh Baron and Rob Lachenauer – What Are the Signs You’re Losing Control of Your Family Business?

This podcast demolishes the myths that family businesses are beset by conflict and poised to fail. Instead, Josh Baron and Rob Lachenauer outline ways that family business owners can learn to practice “active ownership” and thereby materialize the true value that they bring to the business. In this interview with Keith Whitaker, they also discuss the signs that you’re losing control of your family business and what to do about it.

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EPISODE 21: Patricia Angus – Are You Wealthy?

In the first chapter of the book, Patricia Angus tells a fascinating story about a conversation she had with a cab driver about wealth and life and asks the question – “Are you wealthy?” This question may seem at first blush easy to answer, just a quantitative matter. But of course it all depends on what you mean by “wealth”. In this conversation with Tom McCullough, she invites listeners to think through that question in ways far beyond money, including the impact that each of us has on the world around us.

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EPISODE 20: Scotty McLennan – What Are the Most Important Factors in Living Well?

What is the meaning of life? Why are we here? What opportunities–and challenges–does financial wealth pose for living well? These are just some of the questions that Rev. Scotty McLennan takes on in this wide-ranging discussion with Keith Whitaker, which also makes the case that reading well is key to living well.

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EPISODE 19: Jennifer East – How Can You Improve Family Communication?

There are few topics more important and more challenging than family communication. Jennifer East is an advisor to business families and brings unique perspective to the topic. In this conversation with Tom McCullough, Jennifer talks about her own experience growing up in an entrepreneurial family and what she has seen in the many families she has worked with. She offers practical, concrete steps for improving family communication, which come down to good planning, structure, and the courage to take action.

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EPISODE 18: Suniya Luthar and Nina Kumar – How Can You Help Children Thrive in a World Focused on Success?

What greater asset can there be than our children? Yet the desire for “enrichment” can often lead to children feeling pressured by the expectation for achievement. Psychologist Suniya Luthar and her daughter Nina Kumar have studied, written on, and lived the complexities of this experience. In this podcast with Keith Whitaker, they share what parents should look for and practices that they can use to help young children and teenagers navigate the complexity of school, sports, friends, and wealth.

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EPISODE 17: Kirby Rosplock – Should You Choose a Single-Family Office or a Multi-Family Office?

Some families have determined that they could benefit from the integrated objective approach offered by a family office, which then leads to another set of questions such as “Should you choose a single‐ family office or a multi‐ family office?” In this interview with Tom McCullough, family office expert Kirby Rosplock walks us through a thoughtful, reasoned, and personally relevant way to make this decision. She also offers some handy evaluation tools to understand the choices.

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EPISODE 16: Ellen Remmer – What Is the Difference Between Charity, Philanthropy, Strategic Philanthropy, and Impact Investing?

Do you ever worry that you haven’t found your philanthropic “passion”? Ellen Remmer, who has led one of the world’s most innovative philanthropic consulting groups, challenges that concern right from the start of her interview with Keith Whitaker. Ellen talks about philanthropy as a journey that involves much experimentation, with learning from success and failures. She also supplements her chapter’s definition of several key philanthropic terms with special attention to impact investing, which she sees as a way for families to make the most out of all their resources, not just their tax-exempt ones.

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EPISODE 15: Dirk Jungé – Foreword

Dirk Jungé is a leader and pioneer in the family office field, providing leadership to his family’s firm, Pitcairn, for many years. Dirk was kind enough to write the foreword for Wealth of Wisdom. In this episode, he talks to Tom McCullough about how wealth is an amplifier of all things and how, if not properly tended, it can be a family’s undoing. And he tells many stories about experiences of client families and of his own (like “Rock Acres”) that have shaped his views of families and wealth.

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EPISODE 14: Jay Hughes – What Does the Future Hold for Families with Significant Wealth?

Jay can rightly be said to be the founder of the field of family wealth. In this discussion he reflects on the journey that brought him to this work, his current role as an elder, and the paramount importance of elders for families who wish to succeed over generations. Jay also discusses the true meaning of the proverb “Shirtsleeves to shirtsleeves in three generations” (hint: it’s not just about money) and specific practices that families can and must adopt to face a future of radical changes.

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EPISODE 13: Jamie Forbes – How Can You Preserve a Beloved Family Vacation Home or Estate?

There are few assets that generate as much emotional heat as a family vacation home or estate. Jamie Forbes knows the power of family vacation property through his growing up part of the Forbes family, with their shared estate of Naushon Island off Cape Cod, which has been in the family for over 150 years. In this podcast Jamie shares specific practices that his family and others use to strengthen family communication and decision-making. He also talks about what it is like to grow up as a member of a prominent family, both the positive and negative aspects of the experience.

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EPISODE 12: Covie Edwards-Pitt – How Can Your Family Encourage Financial Literacy in Every Member?

This is a question that practically every parent asks, whether or not they have money. But wealth can deprive children of the natural education in financial literacy. Coventry Edwards-Pitt has written an entire book about how successful heirs develop healthy money skills. In this podcast she shares concrete practices that parents can adopt, whether you are parenting young children or adults.

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EPISODE 11: Blair Trippe – How Can You Best Manage Conflict in Your Family?

Conflict is a normal part of family life. But it can be difficult to talk about and to manage, especially when significant wealth or a family business is involved. Blair Trippe is a counselor who has years of experience working with families in conflict. In this podcast Blair defines the different types of conflict, shares strategies for dealing with different forms of conflict, and talks about measuring the “family factor” needed to help families weather the usual slings and arrows that fortune sends their way.

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EPISODE 10: Andrew Hier – Why Is Family Unity So Important and How You Can Achieve It?

Family unity sounds like a good thing, but in this podcast a senior advisor to families, Andrew Hier, argues that unity is in fact vital to the long term success of a family or its enterprise. In his conversation with Tom McCullough, Andrew talks about the corrosive effects of disunity (including disputes, divisions, mistrust, political maneuvering, entropy) that can fester and ultimately crush a family and its enterprise. Thankfully, Andrew also provides practical ideas on how to build and strengthen family unity.

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EPISODE 9: Patricia Annino – How Can You Prepare for Longevity and Mental Incapacity Among Family Members?

With an increasingly aging population, families need to turn their attention (sooner rather than later) to the issues of mental competence. This may refer to the traditional problem of older family members living longer with diminished competence, but also to those who live longer in good shape with sustained competence (-think Queen Elizabeth). Both of these scenarios have significant consequences for families. Tom McCullough talks to lawyer and family advisor Patricia Annino about this critical topic and how families can anticipate and prepare for it.

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EPISODE 8: Philip Marcovici – How Can You Find Trustworthy Advisors?

Life is complicated, and it gets more so as wealth increases. While advisors are almost always necessary, it can be hard to find good one, with the the skills, experience, empathy and integrity you want. And, once found, it can be often difficult to manage them in a effective way that stays focused on the needs of the family. In this podcast, Tom McCullough has a fascinating conversation with Philip Marcovici, a retired lawyer and consultant to global families, about the challenge of finding and keeping effective advisors you can trust.

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EPISODE 7: Alex Scott – Can a Family Stay Together After the Operating Business Is Sold?

In this episode, Tom talks to contributing author Alex Scott, a business leader and a member of a multi-generational family of wealth from the UK. Alex answers the question ‘Can a Family Stay Together After the Operating Business Is Sold?’ with an enthusiastic ‘yes’. But of course that result does not come about without considerable intentionality and effort, so Alex describes some of the practices that worked well for his family and how other families might apply them. Note that this episode has a lot of relevance for families that don’t have operating businesses as well as those that do.

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EPISODE 6: Keith Whitaker – His Thoughts on Wealth of Wisdom

In this special episode of the podcast, Keith Whitaker (Tom’s co-author on Wealth of Wisdom) is interviewed by Scott Dickenson. Scott and Keith discuss Keith’s career, his past books, and his experience working with Tom while writing Wealth of Wisdom. Be sure to listen to the end, where Keith speaks about a few of his favourite essays in the new book, and what he hopes that families get from it.

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EPISODE 5: James Grubman – How Do You Balance Family Stability with Resilience Over the Generations?

In this episode, Tom interviews contributing author Dr. James Grubman on his chapter in the book titled, ‘How Do You Balance Family Stability with Resilience Over the Generations?’. Jim is a psychologist and consultant to multi-generational families about the issues that arise around wealth. He shares from his own experience with families and talks about how they can successfully adapt to changing conditions over time, yet not lose the benefit of the values and skills from the past that got them to where they are today.

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EPISODE 4: Barnaby Marsh – How Can You Wisely Develop a Long-Term Strategy For Your Philanthropy?

In this episode, Tom interviews contributor Barnaby Marsh on his chapter in the book titled, ‘How Can You Wisely Develop a Long-Term Strategy For Your Philanthropy?’. Barnaby is co-founder of the philanthropic services agency, Saint Partners. In this podcast, he reflects on the massive (and probably inevitable) societal changes we are going through, and how you can wisely develop a long-term strategy for your philanthropy in that context.

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EPISODE 3: Heidi Druckemiller – Does Family History Matter?

In this episode, Tom interviews contributor Heidi Druckemiller on her chapter in the book titled, ‘Does Family History Matter?’. Heidi is a senior consultant at The Winthrop Group and suggests that the story of your past can help you to discover your family’s unique values, shape its moral purpose, and direct its strategic decision-making. It will also, inevitably, give your life meaning in ways that you can’t yet imagine.

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EPISODE 2: Scott Hayman – Is It Worth Having a Financial Plan?

In this episode, Tom interviews contributor Scott Hayman on his chapter in the book titled, ‘Is It Worth Having a Financial Plan’. Scott is the President of Northwood Family Office and has been Tom’s business partner for the last 15 years. Scott discusses his thoughts on the benefits of having a financial plan and expands on some of the ideas he brings up in his chapter.

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EPISODE 1: Tom McCullough – A Wealth of Wisdom and Why Should You Read This Book?

In the first episode of the podcast, Tom McCullough is interviewed by his colleague Scott Dickenson on the new book, where the idea for it came from, and how his co-author Keith Whitaker got involved. A great overview of what the book is about, who it is for, and what Tom hopes readers get from it.

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