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Reading List

The Northwood Summer Reading List - 2023

Tom McCullough

I am writing this reading list from Ottawa, where I am a keynote speaker at the 2023 Family Enterprise Canada (FEC) Symposium, a national conference for the family business community. There are attendees from 160 family businesses from across Canada discussing trends and challenges. Family-owned businesses are estimated to generate about 60 percent of Canada's GDP, employ 6 million workers in Canada, and create 70 percent of all new jobs in North America. It’s great to see groups like FEC coming together to lift the knowledge gap around family business.

We are now five months into 2023 and economically things remain stable but still very uncertain – the classic ‘VUCA’ world—volatile, uncertain, complex, and ambiguous. The new interest rate environment is still very fresh, and the impact hasn’t been fully felt. We are starting to see cracks in sectors and companies that were highly leveraged. On the topic of debt, yet another US debt ceiling crisis has come and gone. This is the 4th such "crisis” since 2011. It’s a political football like no other and with American politics as tense as they have been over the last several years, it’s not surprising this one was highlighted politicized. Markets gyrated as the US worked through this crisis, but we see it only as short-term noise.

The US regional banking failures were another significant feature of 2023 and thankfully the contagion has been limited. It’s good to see that federal regulations put in place following the 2008 recession have strengthened the US banking sector overall, but the various states have learned the importance of this regulation the hard way. Speaking of failed banks, Silicon Valley Bank (SVB) highlights the challenge of current ESG standards. SVB was ranked highly by ESG standards, but the G (Governance) was probably questionable. It’s a good reminder that we are still in the early days of ESG standards and reporting frameworks.

Now, let’s talk tech. For many tech startups around the world, it’s a very different environment in 2023. The free-flowing capital propelled by ultra-low interest rates has slowed and many tech companies are struggling to raise money. The period after the bubble and the 2008 recession proved to be very good years for venture capital. Valuations for companies came back down to reality and entrepreneurs become more focused and resilient.

On the AI front, it was surreal to see ChatGPT creator and OpenAI CEO Sam Altman stand up in front of Congress and plead for his industry to be regulated. It’s not often this happens. I went to the source itself (ChatGPT) to lay out the risks of unregulated AI, and it noted these five:

  1. Ethical and social implications: Unregulated AI can perpetuate biases, discrimination, and opacity in decision-making, raising ethical and fairness issues.
  2. Security and privacy risks: Without regulation, AI systems may compromise data security and personal privacy, leading to unauthorized access and misuse of sensitive information.
  3. Economic disruption and job loss: Unregulated AI deployment may result in significant job displacement and economic inequalities if not accompanied by measures to reskill or upskill the workforce.
  4. Autonomous systems and safety concerns: Lack of regulation for autonomous AI systems, such as self-driving cars or autonomous weapons, can pose risks to human lives and require proper oversight.
  5. Manipulation and misinformation: Unregulated AI can be exploited to spread misinformation, manipulate public opinion, and disrupt trust in various contexts.

Well said!

On a more cheerful note, Northwood Family Office celebrated our 20th anniversary on May 25th with a gathering of clients, staff, and friends of the firm in Toronto. We have an amazing group of clients, and grateful for their trust and confidence. We are also fortunate to have such an incredible group of next-gen staff who are enthusiastic and full of new ideas and energy. We have been able to achieve something special over the last 20 years, and I am even more excited about the next 20!

We’ve curated our latest reading list, including interesting books, articles, and some podcast options that might interest you. I hope you enjoy the selection of content below and wish you and your family a wonderful summer.

Click on the titles below to see the full content.

Article Recommendations

New Yorker | The End of the English Major

Enrollment in the humanities is in free fall at colleges around the country. This article addresses the decline of the English Major in favor of more practical and career-oriented disciplines and how the diminishing value of studying literature may have long-term implications for critical thinking and cultural understanding.

El Pais | ChatGPT is just the beginning: Artificial intelligence is ready to transform the world

There has been an endless wave of AI/ChatGPT articles over the last few months – this one was our favorite. It highlights the potential of AI and how it can revolutionize so many different industries, with the potential to reshape the world.

New York Times | ‘The Godfather of A.I.’ Leaves Google and Warns of Danger Ahead

Geoffrey Hinton, a prominent British-Canadian AI pioneer shares why he regrets his work.

Financial Times | Some Quick Takeaways from Bain’s Private Equity Report

A good snapshot of the state of private equity in 2023.

The Atlantic | How Wrestling Made Trump

Not completely surprising, but Trump grew up a wrestling fan and he has relied on WWE tactics during his political career. This is an interesting look into the history.

HuffPost | 30 Questions To Ask Your Kid Beyond 'How Was Your Day?'

This article provides specific and open-ended questions for having meaningful conversations with your children (or grandchildren).

Harvard Business Review | A Two-Minute Burnout Checkup

We have heard it a million times: burnout is devastating. This simple checkup helps us approximate how close we are to our personal limits.

Politico | The Surprising Geography of Gun Violence

A fascinating deep dive into why there is such stark contrast in gun violence between various regions in the US. But even more than that, it outlines a remarkable theory that the contemporary U.S. is actually made up of multiple separate “nations” that have their own unique history and their own ethnographic, religious, and political characteristics, and distinct ideas about the balance between individual liberty and the common good and what the United States should become. It comes from a 2011 book called American Nations: A History of the Eleven Rival Regional Cultures of North America, which I am now reading. Absolutely absorbing!!!

New York Times | Office Workers Don’t Hate the Office. They Hate the Commute

This article touches on Elon Musk’s stance on remote work and why employees are pushing back.

Globe and Mail | Population decrease is irreversible. How will we manage the decline of humanity?

More than 30 countries, including China, are expected to lose half their population this century. This piece talks about why the problems will multiply as societies age and shrink.

Harvard Business Review | Words and Phrases to Avoid in a Difficult Conversation

This article is a couple of years old, but we keep referring back to it when heading into difficult family conversations.

The Atlantic | The Best Cuisine on Earth

The title says it all.

Book Recommendations

Barbara Kingsolver | Demon Copperhead

Set in the mountains of southern Appalachia, Demon Copperhead is the story of a boy born to a teenage single mother in a single-wide trailer, with no assets beyond his dead father's good looks and copper-colored hair, a caustic wit, and a fierce talent for survival.

Amor Towles | The Lincoln Highway

An imaginative story about a highway road trip to California that keeps getting derailed, with an unforgettable cast of characters. Written by the acclaimed author of A Gentleman in Moscow.

Ray Dalio | Principles for Dealing with the Changing World Order: Why Nations Succeed and Fail

A great read for 2023. Dalio examines the factors that contribute to the success or failure of nations in an evolving global landscape. Drawing from historical patterns and his own experiences, Dalio provides insights into the complexities of international relations and offers principles to guide individuals and nations in adapting to the changing world order.

Kristin Keffeler | The Myth of the Silver Spoon: Navigating Family Wealth and Creating an Impactful Life

Using the science of positive psychology, Kristin offers actionable strategies to help individuals who are inheriting wealth (and others) live their best lives. Kristin was also one of the keynote speakers at the Family Enterprise Canada conference last week. She is amazing!

Northwood’s own Scott Dickenson’s 2022 Reading List (10 Books)  

Reader Suggestions:

Hilary Pearson | Charity to Change: Inside the World of Canadian Foundations

Excellent overview of some of the major emerging trends in family foundation philanthropy. Hilary provides thoughtful insight into twenty of our most "strategic and proactive" Canadian foundations as they reflect seven trends she sees as central to this strategic approach.

William MacAskill | What We Owe the Future

In this book, William MacAskill argues that the fate of the world is in our hands. Humanity’s written history spans only five thousand years, but our yet-unwritten future could last for millions more — or it could end tomorrow. Astonishing numbers of people could lead lives of great happiness or unimaginable suffering, or never live at all, depending on what we choose to do today. MacAskill is an associate professor in philosophy at the University of Oxford. At the time of his appointment, he was the youngest associate professor of philosophy in the world and a Forbes Magazine “30 Under 30” social entrepreneur.

Other Recommendations

TV: Triangle of Sadness

Podcast: The History of Sketch Comedy

Video: Amazing mind reader reveals his ‘gift’

Favorite Tweet:

How quickly ChatGPT has gotten to 1 million and 100 million users vs. other technologies.

As a lifelong learner, I am always interested in reading or listening to material that broadens my horizons, challenges my thinking, and provides all-important context for the decisions we make. This is true for the entire Northwood team.

We’d also be interested in hearing what you’ve been reading or listening to lately. If you’ve come across any particularly insightful books, articles, shows, or podcasts, please feel free to send them to me at Thanks to the many people who have already shared their ideas.    

All the best,  



Tom McCullough

Tom McCullough is Chairman and CEO of Northwood Family Office. The combination of his background, along with his own family’s desire for a truly ‘comprehensive, customized and confidential service, led him on a search for a multi-family office. Tom is a frequent speaker on issues relevant to families of wealth and is the co-author of Wealth of Wisdom: The Top 50 Questions Wealthy Families Ask and Family Wealth Management: Imperatives for Successful Investing in the New World Order and the soon-to-be-released Wealth of Wisdom: Top Practices for Wealthy Families and Their Advisors. He is an adjunct professor and Executive-in-Residence at the University of Toronto’s Rotman School of Management MBA program. He is an Entrepreneur-in-Residence at Western University’s Ivey School of Business and a member of the Editorial Board of the Journal of Wealth Management. He was recently awarded ‘Best Individual Contribution to Thought Leadership in the Wealth Management Industry’ by the 2020 Family Wealth Report Awards.

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