A few years ago, I was sitting in a San Francisco boardroom with a family that had recently sold their technology business for just over $400 million. The patriarch—a self-made entrepreneur who had spent 28 years building the company from a garage startup—was visibly exhausted. Not the exhaustion of someone who had just finished a sprint. Something heavier. The kind that sets in when adrenaline finally stops doing its job and reality moves in.
He slid a legal pad across the table toward me. On it, in neat handwriting, was a list of 10 items. “These,” he said quietly, “are what I can’t stop thinking about.”
Not one of them was about the stock market.
That moment has stayed with me for years, and not because it was unusual. It stays with me because it was so utterly typical—and yet so few advisors in this industry are prepared to handle what was on that list. His concerns ranged from whether his son had the temperament to lead the family trust, to whether his daughter, who lived in New York, understood that her U.S. citizenship created an entirely separate tax exposure. He worried about a former business partner who still held a grudge. He worried about cybersecurity. He worried about what his grandchildren would do with money they never had to earn. He worried, in the final item on the list, about what his legacy would actually mean—not in financial terms, but in terms of the family he was leaving behind.
Over more than three decades in wealth management—from early roles at Merrill Lynch and CIBC World Markets, through my years at Morgan Stanley where my team at Graystone Consulting ranked #1 in California and #8 in all of North America on Barron’s Top 50 Institutional Consultants list, advising on more than $20 billion USD in assets—I have sat across from hundreds of UHNW families.
In nearly half of family-business transitions, the founder simply can’t step away. My answer: bring in a third-party consulting or advisory group so the potential transition goes even better than I could facilitate.
What I’ve learned is that the things that genuinely worry UHNW families are rarely the things that dominate financial headlines. The real worries are messier, more personal, and far harder to solve with a rebalancing trade. The market recovers. Family mistakes often don’t. Here, in no particular order of urgency, are the first five of 10 worries that come up again and again.
1. Succession without a plan
Only 53 per cent of family offices globally have a wealth succession plan in place, according to the UBS Global Family Office Report 2025. Almost a third are deliberately deferring—not because the problem isn’t real, but because they believe there’s plenty of time. There isn’t.
I’ve seen this pattern more times than I can count. The patriarch who built the business from nothing quietly assumes his children understand what he’s built, what it took, and what he wants for it. They often don’t. And when something unexpected happens— illness, a dispute, a market shock—the absence of a succession plan doesn’t just create inconvenience. It creates irreversible damage. I worked with a family a number of years ago where the founder passed unexpectedly at 71—relatively young and in excellent health until he wasn’t. He had a will. He had an estate plan. What he did not have was any articulation of how decisions should be made among his three children going forward. Within 18 months, two of them were not speaking to each other. The business—still operating—had lost two key executives who couldn’t navigate the family tension. The estate was largely intact on paper. The family was in ruins.
What makes this worse: Of those families who do have a plan, only 26 per cent actually consulted the next generation from the outset. That’s not succession planning. That’s a document gathering dust in a binder on a shelf.
Real succession planning involves conversations that are uncomfortable, clear-eyed, and sometimes painful—about who is actually ready, who isn’t, who has the temperament and who has the capability, and what happens when those two things diverge.
Thane Stenner
It requires honesty about the gap between a founder’s emotional attachment to the business and the cold logic of who should actually run it. The families who navigate succession well do it early, do it iteratively, and do it with professional facilitation. They treat it as a multi-year process, not a document. The ones who defer—regardless of how sophisticated their investment portfolios are—are playing a game of Russian roulette with the most valuable thing they’ve spent their lives building.
2. The next generation and motivation
This one is rarely spoken out loud in the first meeting. But it’s everywhere. Sixty-one percent of UHNW individuals express concern that family wealth will undermine their heirs’ personal drive for success, per the Bank of America 2026 Study of Wealthy Americans. That figure does not surprise me. The ones who never mention it in a first meeting bring it up eventually—usually in the car on the way home from a meeting they thought was about asset allocation.
The children grow up amid private jets and multiple homes and seamlessly funded lifestyles, and the question becomes: what are they working toward? I’ve sat across from second-generation members who are technically employed but functionally retired in their early thirties—drawing a comfortable allowance, showing up to family meetings, circling the drain of a life without real stakes. I’ve also sat across from G2 family members who have done extraordinary things precisely because they had the platform that wealth provided—who launched businesses, drove philanthropic initiatives, and built legacies that stood independently of their inheritance. The difference between those two outcomes is rarely the amount of money involved. It’s the intentionality—or the complete lack of it—around how wealth is introduced, explained, and governed across generations.
Preparing heirs is not the same as spoiling them, but the line between the two is razor thin, and it shifts depending on the child. Some children are galvanized by early exposure to responsibility. Others are paralyzed by it. Some need to earn something independently before they can value what they stand to inherit. Others integrate remarkably into the family enterprise from a young age. The point is that this requires thought, structure, and often professional guidance. I’ve watched families address this brilliantly through structured internships in the operating business, real decision-making authority—with real consequences—in family investment committees, and age-appropriate financial education that starts well before adulthood. I’ve watched other families assume it would just sort itself out. It rarely does. Purpose doesn’t self-install. It has to be cultivated deliberately, across generations, and often against the headwinds of abundance.
3. Tax exposure and policy risk
The tax environment in both Canada and the United States has rarely been more uncertain—and the families who are most exposed are those who have structured themselves once and assumed those structures would hold. They don’t always. Capital gains inclusion rate changes, proposed estate tax reforms, intergenerational trust structures under political pressure—the legislative landscape shifts faster than most families can adapt their structures, especially when those structures are complex.
The danger isn’t just the tax itself. It’s the surprise. A family that has spent 20 years optimizing around one set of rules can find those rules amended in a budget overnight. I’ve watched families absorb material financial damage not because they were poorly advised, but because their advisors were reactive rather than proactive—waiting for the legislation to pass before modelling the implications, rather than running scenarios in advance. That matters enormously in the window between announcement and implementation, which is often where the real planning opportunity lies.
Cross-border families—and there are many in the Canadian UHNW community—face dual exposure that compounds this risk significantly. Canadian tax residency rules on one side, U.S. estate tax thresholds and citizenship-based taxation on the other. A Canadian citizen with an American-born spouse and a child who took a U.S. green card a decade ago faces a web of obligations that very few advisors fully understand. The interaction between Canadian deemed-disposition rules and U.S. estate tax can produce outcomes that shock even experienced families when they finally model them explicitly. The families who manage this best aren’t the ones who are most aggressive in their tax optimization. They’re the ones who are most proactive—running scenario analyses before the budget drops, not scrambling after it. They’re the ones who have a tax advisor, an estate lawyer, a cross-border specialist, and an investment advisor who are all in the same conversation, not operating from separate islands of expertise. The cost of coordination is trivial compared to the cost of a tax ambush that nobody saw coming because no one was watching the whole picture at once.
4. Concentration risk in a single asset or company
This may be the hardest conversation in wealth management. Full stop. A founder who built a company worth $200 million over 30 years, with 75 per cent of their net worth sitting in that one position. They know the risk intellectually. They’ve heard the arguments. They’ve nodded along. And then they don’t move. The company is their identity. It’s the thing that validated the risk they took, the sacrifices they made, the years they missed with their children. Selling a meaningful portion of it feels less like financial planning and more like a kind of self-erasure.
I understand that. I genuinely do. But the math is brutal and unforgiving.
One bad quarter, one regulatory shift, one key customer defection, one technological disruption that reframes the entire competitive landscape, and decades of wealth accumulation can be permanently impaired.
Thane Stenner
I’ve sat across from brilliant executives—people who understood capital markets, understood risk, had built durable businesses—who watched their concentrated positions erode in ways they never imagined possible. People who knew better and still couldn’t act. Not because they were irrational, but because the emotional attachment to a concentrated position can override rational analysis in ways that almost no other financial decision does.
The tools for managing concentration risk have become genuinely sophisticated. Exchange funds. Monetizing collars. Charitable remainder trusts that accomplish both diversification and philanthropic objectives. Structured dispositions that spread the tax event across multiple years. The execution playbook is well-developed. What remains difficult is the decision to engage with it at all—and that’s a conversation that requires a relationship with enough depth and trust that the advisor can be direct about something the client doesn’t want to hear. Diversification isn’t an opinion about the company’s quality. A concentrated position isn’t a portfolio. It’s a bet—and no matter how informed and reasonable that bet is, a single position carries a category of risk that no amount of conviction can fully hedge. The families who understand this and act on it systematically—even partially, even incrementally—tend to sleep better. They also tend to retain their wealth across the generations that follow.
5. Geopolitical volatility and portfolio resilience
Over two-thirds of family offices named a global trade war as their top near-term risk in 2025, and when asked about the five-year horizon, 61 per cent flagged major geopolitical conflict and 53 per cent flagged global recession as primary concerns, according to the UBS Global Family Office Report 2025. Tariff shocks. Currency dislocations. Supply chain fragmentation. The reconfiguration of trade relationships that defined the post-Cold War order. None of this is hypothetical anymore. These are live conditions affecting real portfolios, real operating businesses, and real family wealth—not tail risks to be noted and discounted.
And yet, the data from that same report shows something that should give every thoughtful UHNW investor pause: U.S. family offices have virtually withdrawn from international markets, with 86 per cent of assets held domestically, up from 74 per cent just five years ago. That is a remarkable concentration of capital in a single jurisdiction at exactly the moment when the risks inherent in that jurisdiction—political polarization, regulatory unpredictability, dollar dominance under challenge—are most elevated. I am not making a case for wholesale reallocation out of North American assets. I am making the case that an 86 per cent domestic weighting is not a considered position. It’s an artifact of home bias compounded over time, rationalized after the fact.
The families I work with who have navigated geopolitical volatility best share a common approach: they think in terms of the geographic distribution of their risk, not just the diversification of their asset classes. They hold real assets in multiple jurisdictions. They maintain meaningful allocations to non-dollar-denominated positions. They invest in resilience—businesses and assets that are less tightly coupled to any single political or regulatory environment. A North American-only mentality may have been defensible in calmer times. In a world that is actively reshaping its economic architecture, with alliances fracturing and new trade blocs emerging, it is a structural vulnerability hiding in plain sight. Recognizing it is the first step. Building a portfolio that reflects the world as it actually is—rather than as it was 20 years ago—is the work that follows.
Next week: Worries 6-10 and the common thread that ties all 10 together.
About the author
Thane Stenner, CIM®, FCSI® is a Senior Portfolio Manager and Senior Wealth Advisor, and the founder of Stenner Wealth Partners+ at CG Wealth Management (Vancouver, BC / Toronto, ON). He is the host of Smart Wealth™ with Thane Stenner on BNN Bloomberg, and the Founding Member, Chairman Emeritus and former Managing Director of TIGER 21 Canada—the premier peer membership organization for ultra-high-net-worth individuals in Canada.
Prior to founding Stenner Wealth Partners+, Thane served as Managing Director, International Client Advisor, Institutional Consulting Director, Alternative Investments Director, and Portfolio Manager at Morgan Stanley Wealth Management, where he led the StennerZohny Group of Graystone Consulting—a division of Morgan Stanley with $336 billion USD in assets under management. His team advised on more than $20 billion USD in assets and was ranked #1 in California and #8 in all of North America on the Barron’s Top 50 Institutional Consultants list (2020). Earlier in his career, Thane held senior roles at Merrill Lynch International Private Client Group, CIBC Wood Gundy (World Markets), and Richardson GMP.
Thane has been recognized among Canada’s Top Wealth Advisors by the Globe and Mail and SHOOK Research, ranked #6 nationally on Wealth Professional’s Top 50 Advisors list, and Stenner Wealth Partners+ was named Wealth Professional’s Top Wealth Advisory Team in June 2026. He is dual-licensed under both CIRO (Canada) and FINRA (United States).
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About Stenner Wealth Partners+
Stenner Wealth Partners+ (SWP+) is an in person/virtual Multi-Family Office/Outsourced CIO Consulting team of financial/wealth specialists with a boutique approach and global perspective. SWP+ serves Canadian and US investors/households with generally a minimum of $10M+ in investable assets (or $25M+ net worth). As a CG Wealth Management team, SWP+ is a highly exclusive practice team with one of Canada’s largest independent wealth management firms. Client range of net worths: between $25M and $3B+. They strategically limit new client engagements, onboarding a select number of new key relationships annually to ensure a highly personalized and focused approach. SWP+ is a member of Canadian Family Offices.
Disclaimer: This story was created by Canadian Family Offices’ commercial content division on behalf of Stenner Wealth Partners+ at CG Wealth Management, which is a member and content provider of this publication. CG Wealth Management is a division of Canaccord Genuity Corp., member of CIPF and CIRO. Tax & Estate advice offered through Canaccord Genuity Wealth & Estate Planning Services Ltd. Thane Stenner’s views, including any recommendations, expressed in this article are his own only, and are not necessarily those of Canaccord Genuity Corp.