The Perspective Blog
The Northwood 2025 Winter Reading List
Welcome to our Winter Reading List.
As we step into another season of change and opportunity, I find myself reflecting on the many things I’m proud of at Northwood:
- Our team—for once again being nominated for the Family Wealth Report Multi-Family Office Award in 2025, a testament to the work we do every day.
- Our next generation of leaders—who are stepping up as we continue to thoughtfully transition leadership and management at Northwood.
- Our commitment to strategic priorities—from investments and technology to advancing women in family offices, continuously making the firm stronger for both our clients and our team.
- Our culture of curiosity and enthusiasm—which fuels us daily and reminds me that the future is bright.
Outside our walls, the world continues to be surprising. Ongoing tariff disputes and economic pronouncements coming from the White House have sparked no shortage of economic uncertainty. Trump sees himself as the gatekeeper of the world’s greatest bazaar, determined that the U.S. government should take a cut of every deal. Whether these moves signal lasting changes or just noise remains to be seen—but in times like this, disciplined, long-term planning matters more than ever.
And then there are the “51st state” remarks, a reminder of how important it is to preserve Canada’s distinct identity, values, and political system. As Canadians, we’re proud to chart our own course. That said, we are also a moon to Planet America—unavoidably shaped by its gravity.
One of the other big forces reshaping society today is AI. It’s a thread you’ll see woven throughout this reading list, including a great podcast on surviving the AI endgame. As Jerry Seinfeld recently quipped: “We’re smart enough to invent AI. Dumb enough to need it. And so stupid we can’t figure out if we did the right thing.” It’s a perfect summary of the paradox we’re all living in.
With that, we’re excited to share our latest reading list—a curated mix of books, articles, streaming recommendations, and thought-provoking content we’ve been talking about around the office. We hope you enjoy it—and as always, we welcome your thoughts.
Click on the titles below to see the full content.
Article Recommendations
The Atlantic | How Life Became an Endless, Terrible Competition
Daniel Markovits dives into how our meritocratic society, designed to reward talent and effort, has ironically led to increased inequality and a relentless rat race, making everyone—from the rich to the middle class—miserable.
CFA Institute | Dispelling Myths About the 'Great Wealth Transfer'
This piece challenges common assumptions about the massive wealth transfer from baby boomers to millennials, highlighting that the reality may be more nuanced.
Substack | The New Colonialism: Power, Data, and the Transformation of Human Experience - Tripp Fuller
This article explores how digital platforms are reshaping human experiences, drawing parallels to historical colonialism by extracting and exploiting user data, leading to significant imbalances in power and knowledge.
Substack | Blame Canada
A chilling read where Timothy Snyder argues that Trump and his allies are using absurd lies—like blaming Canada for the U.S. fentanyl crisis—to shift blame and create propaganda that could justify extreme actions, even annexation.
NPR | How Will Australia's Under-16 Social Media Ban Work? We Asked the Law's Enforcer
NPR discusses Australia's new law banning social media access for those under 16, exploring its enforcement challenges and potential implications for online youth safety.
Collab Fund | The Three Sides of Risk
5 years old now, but one of our favorites—Morgan Housel breaks down risk into three dimensions—the odds you will get hit, the average consequences of getting hit, and the tail-end consequences of getting hit. Offering a different perspective on decision-making and uncertainty.
The Atlantic | How Hitler Dismantled a Democracy in 53 Days
A chilling reminder of how democracies can erode from within under the guise of legality.
The Atlantic | Why the Past 10 Years of American Life Have Been Uniquely Stupid
We had this on our list in 2022 but came back to it again. It examines how social media has fragmented society, eroded trust, and contributed to a decade marked by increasing stupidity and polarization.
Book Recommendations
From deep insights on family business and personal growth to gripping sci-fi and timely takes on tech, here’s what’s been on our bookshelves lately:
Big Ideas and Bold Thinking
The Enduring Enterprise by Devin DeCiantis and Ivan Lansberg
This book dives into how family businesses in emerging markets thrive amid chaos—war, economic crises, even climate disasters. As global instability grows, their lessons on resilience, adaptability, and long-term thinking are more relevant than ever.
Sapiens by Yuval Noah Harari
A sweeping, accessible history of humankind—from our caveman roots to modern life—that makes you think differently about everything from money to religion to the future of AI.
From Strength to Strength by Arthur Brooks
This one’s for anyone thinking about legacy and meaning. It’s about how to pivot from chasing success to embracing purpose as we age—encouraging, wise, and worth revisiting.
Reset: How to Change What's Not Working by Dan Heath
This brand new book, from one of our favorite authors, explores a framework for getting unstuck and making changes that matter. The secret is to find “leverage points”: places where a little bit of effort can yield a disproportionate return.
Switch: How to Change Things When Change Is Hard by Chip Heath and Dan Heath
A practical guide to making change stick—at work, in teams, or in your own life. Full of real-world examples and surprisingly fun to read. A classic.
Rework by Jason Fried & David Heinemeier Hansson
Forget business school—this short, punchy read is full of counterintuitive but ultra-practical advice on building a business in today’s world. Perfect for entrepreneurs and changemakers alike.
Power, Technology & the Future
Chip War by Chris Miller
A gripping look at the global battle over semiconductors—the tiny chips that power everything from smartphones to fighter jets. Eye-opening and essential to understanding 21st-century geopolitics.
The Nexus Trilogy by Ramez Naam
Imagine a mind-enhancing drug that links brains together—and the global chaos that follows. Fast, futuristic, and wildly entertaining (start with Nexus, then Crux and Apex).
History & Memoir
Tuesdays with Morrie by Mitch Albom
A touching true story about a former student reconnecting with his dying professor. It’s a conversation about what really matters in life—love, purpose, and letting go—with timeless lessons for any generation. An old classic.
A World Lit Only by Fire by William Manchester
A vivid, often brutal journey through the Middle Ages. If you like your history raw and unfiltered, this one’s for you.
Greenlights by Matthew McConaughey
Equal parts memoir and motivational guide, this is McConaughey in full swagger mode—offbeat, insightful, and surprisingly profound.
Born a Crime by Trevor Noah
Trevor Noah’s unlikely path from apartheid South Africa to the desk of The Daily Show began with a criminal act: his birth. Trevor was born to a white Swiss father and a black Xhosa mother at a time when such a union was punishable by five years in prison. The compelling, inspiring, and funny story about his coming-of-age, set during the twilight of apartheid and the tumultuous days of freedom that followed.
Streaming Recommendations
With so much to choose from, it’s hard to know what’s worth your time. While the Golden Age of TV may be behind us, there’s still plenty of great content out there—especially from Apple TV+, which continues to deliver smart, well-produced shows. Here’s what’s currently on our radar.
TV Picks
Shrinking (Apple TV+)
A therapist starts telling his clients the unfiltered truth—with chaotic, heartwarming results.
Slow Horses (Apple TV+)
MI5’s outcasts tackle gritty intelligence work under the leadership of a brilliantly rude Gary Oldman.
Silo – Season 2 (Apple TV+)
In a dystopian underground society, secrets about the outside world begin to unravel.
Severance – Season 2 (Apple TV+)
Work-life balance gets eerie in this mind-bending series about splitting consciousness.
Bad Sisters – Season 2 (Apple TV+)
A dark Irish comedy about five sisters in Dublin being investigated for the death of their toxic brother-in-law. Season 2 isn’t as good as Season 1 but we still loved it.
Movies and Documentaries
Conclave
A suspenseful Vatican drama where cardinals gather to elect the next pope—full of intrigue and hidden agendas.
A Real Pain
A dark comedy about two cousins traveling through Poland to reconnect with their past—and each other. Loved it!
Anora
A gritty love story between a stripper and a Russian oligarch’s son, full of sharp twists and emotional weight.
The Brutalist
Adrien Brody stars as a Holocaust survivor and architect making a new life in postwar America. Beautiful, brooding, and cinematic. Mixed views on this one in the office.
Buy Now (Netflix)
An eye-opening documentary on how big brands like Apple and Amazon manipulate consumer behavior through subtle (and not-so-subtle) tactics. Referred by a reader of this Reading List. Thanks.
Podcast Recommendations
With over 100 episodes, this podcast dives into thoughtful family wealth management—covering everything from governance and legacy to decision-making and values.
(OK, we may be a little biased)
The Prof G Pod with Scott Galloway
Business insights with an edge. Galloway mixes sharp takes on markets and tech with practical life advice—smart, snappy, and often pretty funny.
A nostalgic and entertaining podcast from The Ringer where Bill Simmons and guests break down movies that are endlessly rewatchable. Great for movie buffs and casual viewers alike.
The History of English Podcast
We are up to Episode 182 and still loving it. Alert! Probably suitable only for history, etymology, and grammar nerds. (Stay strong!)
Industry podcasts (where Tom McCullough, Chairman & CEO, has been a recent guest)
Views from the Market – Mario Nigro, Stikeman
Global Wisdom Talks – Jan Petke, C100
Safe Space – Francesco Lombardo, Veritage
Tank Tanks – Matt Cohen, Ripple Ventures
Legacy Builders – Cory Gagon, Beacon
Who We Remember – Jamie Yeunger, StoryKeep
FOXCast CEO Series – Family Office Exchange, Peter Moustakerski
Other Worthwhile Watches
David Frum on America’s Lonely Future & Trump’s “Predatory” Foreign Policy (YouTube)
A thought-provoking interview on the future of U.S. global leadership.
Dan Heath – “How to Find Bright Spots” (YouTube)
A short, inspiring talk on spotting what’s working—and building on it.
Miscellany
As lifelong learners, we are always interested in reading or listening to material that broadens our horizons, challenges our thinking, and provides an 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 us at tm@northwoodfamilyoffice.com, bcj@northwoodfamilyoffice.com or sd@northwoodfamilyoffice.com.
Thanks to the many people who have already shared their ideas.
All the best,
Tom, Brad & Scott