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Six Canadian family-office leaders and the books that energized them

Tomes both classic and new that inspired them professionally and, in some cases, personally

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Family offices help clients manage their wealth, navigate complex financial and legal concerns and create succession plans.

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But keeping up with all these details can leave little time for professional development and staying abreast of fresh ideas in their field. One way to keep up is reading books.

We asked a few Canadian family-office leaders to share the books that have been influential to them. Some are directly related to their fields, and others have helped in career building.

One relatively new book that was mentioned often is Wealth of Wisdom: The Top 50 Questions Wealthy Families Ask, by Tom McCullough, chairman and CEO of Northwood Family Office in Toronto, and Keith Whitaker. The pair draw on the expertise of industry professionals to answer the questions that family office clients should ask their trusted advisors.

Here are a few other titles that family office leaders recommended.

Douglas Byblow
Douglas Byblow

Douglas Byblow, president, Forthlane Partners, Calgary

  • Entrusted: Building a Legacy That Lasts (by David R. York and Andrew L. Howell): “This book provides family office executives and families of wealth with an effective, easy-to-read overview of the foundational purpose for the work that we do. The authors explain the importance of focusing on a process that emphasizes the less tangible and underlying issues and objectives of families as we seek to support and be of service to them. It was recently recommended to me by another experienced family office executive and was a healthy reminder of the value that we can provide when we don’t lose sight of what truly matters to families. (Spoiler alert – what matters is a lot more than just minimizing taxes or maximizing investment returns).”
  • The Right Side of the Table: Where Do You Sit in the Minds of the Affluent (by Scott Fithian and Todd Fithian): “Using a conference room table as a metaphor, the authors illustrate the differing mindset, approach and skills required of professionals who interact with families of wealth depending upon where they sit around a table. Sellers (of investments, products, etc.) are seated across from the family, and professional technicians (e.g. lawyers, tax planners, etc.) are along the sides. Advisors such as family office executives sit adjacent to the family on the same side of the table to deliver trusted, objective support. While each position around the table serves a purpose, the authors helped me to recognize and reinforce that I was best suited for, and most interested in, roles where I can be that objective, trusted advisor and add value by sitting on the same side of the table as the family.”

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Chris Clarke
Chris Clarke

Chris Clarke, CEO, First Affiliated Holdings Inc., and author of True Family Wealth: Love, Money and an Inspired Life, Collingwood, Ont.

  • Strangers in Paradise: How Families Adapt to Wealth Across Generations (by James Grubman): “This is an excellent addition to the tool kit for improving family communication with a view to successful family meetings.”
  • My Stroke of Insight: A Brain Scientist’s Personal Journey (by Jill Bolte Taylor): “A fascinating book about how the human brain functions that has one considering the truth of reality, which is not what our senses tell us it is.”

Scott Dickenson
Scott Dickenson

Scott Dickenson, director of client services, Northwood Family Office, Toronto

  • Range: Why Generalists Triumph in a Specialized World (by David Epstein): “This book presents a fascinating counter-argument to the ‘10,000-hour rule’ popularized by Malcolm Gladwell, which says that it takes 10,000 hours of intensive practice to achieve mastery of complex skills and materials. Epstein argues that in a world that is increasingly hyperspecialized, it is generalists with a broad range of experiences and interests who will ultimately find the most success. As someone who was a late bloomer from a career perspective, the ideas in this book resonated a great deal with me. The opening chapter comparing Tiger Woods (specialist) and Roger Federer (generalist) is worth the price of admission by itself.”
  • Wealth of Wisdom: The Top 50 Questions Wealthy Families Ask (by Tom McCullough and Keith Whitaker): “This one might seem self-serving – Tom signs my paycheques, after all – but my experience over the past few years suggests that this book is becoming the bible for advisors who work with high-net-worth families. Wealth of Wisdom covers a wide range of relevant topics, bringing in more than 50 global subject matter experts to write about their specialties. As editors, Tom and Keith do a great job of setting the stage, but the real value in the book is the access it provides to thought leadership on questions that matter to wealthy families. I also strongly recommend the Wealth of Wisdom podcast, in which Tom and/or Keith interview a different contributor each episode.”

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Éric Lapointe
Éric Lapointe

Éric Lapointe, founder and CEO, CEOS Family Office, Montreal

  • The Go-Giver: A Little Story About a Powerful Business Idea (by Bob Burg and John David Mann): “This recommendation is for my family office peers, and for anyone looking for self improvement, fulfillment and purpose. Choosing to build a multi-family office helped me find my purpose. I had felt lost for 11 years in the world of finance when I found a book about family offices on the internet. Pure luck? I’m not sure, but it was the beginning of a new life. The Go-Giver is about looking for a purpose, and the idea that giving without expecting anything in return is a great way of life. This is a must-read for anyone who wants to live a simple life of greatness by only giving. Don’t worry, if you try long enough (patience!) you will find out that you are not alone, and that life is amazing in its simplest way.”
  • The Adaptation Advantage: Let Go, Learn Fast, and Thrive in the Future of Work (by Heather E. McGowan, Chris Shipley, et al.): “For me The Adaptation Advantage is the greatest book about the future of the multi-family office, even if it’s not about multi-family offices! We spent the last 10 years building what we call today the “human hub,” regrouping most financial and professional services to work as one team with one fee, no sales. The Adaptation Advantage describes the reasoning behind this way of thinking. The only way to understand it is to unlearn in order to relearn; we need to “reset” our brains. As technologies evolve faster and faster, the future for humans is to understand the needs of others. As we move from a complicated world to a complex world, the “human hub” is the last line of defense, where flexibility gives you the ability to pivot from one tool in your toolbox to another, or from one approach to another.”

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Gregory Moore
Gregory Moore

Gregory Moore, partner, Richter Family Office, Toronto

  • “I think you will find that many of us in this space will recommend Family Enterprises – The Essentials, by Peter Leach. Peter is a leading authority in the space of family businesses and the unique attributes of family enterprises. That said, James Hughes’ book Family Wealth – Keeping it in the Family is also exceptional.

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  • “As far as a book that influenced my career in some way, most recently the books of Simon Sinek have been a significant influence on me. His book Start With Why: How Great Leaders Inspire Everyone to Take Action speaks to the value of understanding why some businesses are more innovative and successful than others based on the premise of simply understanding the guiding principals of why your business exists. These are great lessons for family-owned businesses who could benefit from understanding what guiding principles motivate their enterprise and why articulating these clearly can help both the business and the family navigate through periods of uncertainty.”

Arthur Salzer
Arthur Salzer

Arthur Salzer, founder and CEO, Northland Wealth Management Inc., Oakville, Ont.

“Let me share with you my four favourite books that can provide incredible amounts of wisdom and guidance, helping our families prevent the ‘shirtsleeves to shirtsleeves in three generations’ adage. I have been fortunate enough to have either met or know these authors personally. Each book either covers the financial capital or human capital of a family or a combination of the two. Education, governance and the effective management of financial and human capital is imperative for the success of a family over generations.”

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  • The Stewardship of Wealth: Successful Private Wealth Management for Investors and Their Advisors, by Gregory Curtis
  • The Complete Family Office Handbook: A Guide for Affluent Families and the Advisors Who Serve Them, by Kirby Rosplock
  • Family: The Compact Among Generations: Answers and Insights From a Lifetime of Helping Families Flourish, by James E. Hughes Jr.
  • Family Capital: Working With Wealthy Families to Manage Their Money Across Generations, by Gregory Curtis
  • Atlas Shrugged, by Ayn Rand: This book, and her previous work, The Fountainhead, had a great effect on my life. The insights into the current world, politics and the challenges that family enterprises face are prescient. My only regret was not reading this book until I was 40 years old.

Responses have been edited for clarity and brevity.

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