As I noted last week, 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, is the back half of the 10 worries that come up again and again—and the common thread that ties them all together.
6. Cybersecurity and family data vulnerability
UHNW families are among the most targeted individuals on the planet for sophisticated cybercrime—not because they are careless, but because of the inherent complexity of their lives. Multiple properties. Multiple advisors. Multiple legal entities. Multiple family members across multiple generations, each with their own devices, habits, and levels of digital hygiene. The attack surface is enormous, and the stakes attached to a successful breach are extraordinary.
According to Deloitte’s 2024 Family Office Cybersecurity Report, 57 per cent of North American family offices experienced a cyberattack in the preceding 24 months, with 93 per cent of attacks using phishing as the primary vector. These are not crude Nigerian prince emails. The current generation of attacks is sophisticated, personalized, and increasingly AI-assisted. AI-generated deepfake audio impersonating a trusted advisor requesting an urgent wire transfer. A fraudulent email thread that is indistinguishable from an actual conversation between an accountant and a client—constructed from months of compromised email history. A family office employee who clicks a link in what appears to be a routine document from the family’s law firm, and inadvertently grants access to the entity’s entire financial infrastructure.
The weakest link is rarely the institution. It’s a family member who clicks the wrong link at 11pm on their phone. It’s the household manager who has access to the family’s shared drive and uses the same password she uses for everything else. It’s the 22-year-old heir whose social media presence has effectively mapped the family’s entire network of relationships for anyone patient enough to read it carefully. Most advisors never raise this topic in a wealth meeting. They should. Cybersecurity for UHNW families is not an IT problem. It is a wealth preservation problem—as serious, as specific, and as in need of professional management as any other dimension of the family’s financial life. The families who take this seriously engage dedicated cybersecurity firms that specialize in private clients, run regular simulated phishing exercises across the entire family, and treat digital hygiene as part of the family governance protocol, not an afterthought.
7. The family governance gap
Most families accumulate wealth far faster than they build the structures to protect and transmit it. No family charter. No investment policy statement. No defined decision-making process that survives the transition from one generation to the next—or even the transition from one family configuration to another through marriage, divorce, or the introduction of in-laws whose values and financial instincts may be entirely different from those of the family that built the wealth.
While the founder or matriarch is alive and operating, this gap is largely invisible. Their authority, their judgment, their sheer force of personality fills it. They make the decisions, resolve the conflicts, set the tone. The governance structure is, effectively, a single human being. The moment they are gone—or the moment their health declines to the point where that authority becomes ambiguous—the absence of governance becomes catastrophic. Siblings disagree about the investment mandate. One heir wants to take distributions, another wants to reinvest. One wants to sell the ranch that the family has held for 40 years, another considers it sacred. One wants to expand the philanthropic mission, another is skeptical of giving at all. Without a structure to channel those differences—a process, a documented framework, an agreed-upon mechanism for resolution—they become conflicts. Family conflicts, unlike market corrections, do not recover on their own over time. They compound.
Most families accumulate wealth far faster than they build the structures to protect and transmit it.
I’ve watched families that had every financial advantage imaginable fracture along governance fault lines that could have been addressed years earlier for a fraction of the cost of the litigation that eventually followed. And I’ve watched families that built their governance infrastructure deliberately—a family council with real authority, a clear investment policy statement, a family constitution that articulated values and decision rights, and regular family meetings with professional facilitation—navigate extraordinary complexity and disagreement without losing cohesion. The ones who build this infrastructure before it’s needed are the exception. They are also the ones whose wealth survives generational transitions intact.
8. Advisor dependency and fee opacity
Who actually knows everything about your financial life? Not the broad strokes—the actual specifics. Every entity, every trust, every insurance policy, every advisor relationship, every embedded fee, every cross-border exposure, every tax position, every estate planning election that was made and may or may not have been revisited in light of legislative changes since it was put in place. In most UHNW situations, the honest answer is: no one.
The estate lawyer doesn’t know the investment strategy. The investment manager doesn’t know the full trust structure. The accountant doesn’t know the insurance picture. The insurance advisor doesn’t know the alternative investment portfolio. Having advisors operate in silos isn’t just inefficient—it’s genuinely dangerous. I’ve seen situations where a family was paying for essentially the same service from two different firms, neither aware of the other. I’ve seen trust structures that were tax-efficient in isolation become tax-inefficient when combined with the investment strategy being run alongside them, because no one had ever modelled them together. I’ve seen insurance coverage that was redundant in one dimension and dangerously inadequate in another, because the overall picture had never been assembled in one place.
Layer on top of that the question of fees. Do you know exactly what you are paying—in total, across every relationship, including embedded costs, fund expenses, management fees at the entity level, transaction charges, and the economic cost of complexity itself? Most clients don’t—and I say that without any suggestion of impropriety. The fragmentation is structural. It is the accumulated result of decisions made at different times for different reasons, none of which seemed unreasonable in isolation. But the aggregate effect is expensive, opaque, and genuinely risky. A truly coordinated advisory relationship—one where a single senior advisor has full visibility across the entire financial picture and takes responsibility for the coherence of the whole—is rarer than it should be at this level of wealth. It’s also, in my experience, one of the highest-value things a UHNW family can secure.
9. Longevity and the extended retirement challenge
Ninety-two percent of wealthy individuals surveyed by Bank of America in 2026 said longevity is an important factor in their wealth planning. That number is not surprising. What is surprising is how rarely portfolios are actually constructed to reflect it—and how many retirement income strategies I see that were designed for a world where 85 was considered a long life.
Living to 95 is no longer an edge case for a healthy, affluent couple. It is increasingly a base case. That means a 30-year retirement—potentially for both spouses, potentially overlapping—with a cascade of compounding challenges that most retirement models underweight: escalating healthcare costs that accelerate in the final decade of life, long-term care considerations that can run to seven figures in aggregate, possible cognitive decline that creates vulnerability at exactly the moment when good financial decision-making matters most, and inflation eroding purchasing power across multiple decades in ways that are easy to dismiss at 65 and genuinely alarming at 82.
The portfolio that was designed for a 20-year retirement becomes dangerously underfunded at year 25. The withdrawal rate that looked conservative at 65 becomes aggressive by 80—particularly when real-return assumptions from the original plan have failed to materialize, or when inflation has run persistently above the assumed long-term average. I’ve sat with families who are technically wealthy—substantial assets, no immediate concern—but who are nonetheless running a model that will not hold to age 95 without meaningful adjustments. Sometimes the adjustment is structural: the portfolio needs to be repositioned to generate more reliable income with better inflation protection. Sometimes it’s behavioral: the withdrawal rate needs to be recalibrated now, not after it becomes a crisis. And sometimes it requires an explicit plan for late-life care and cognitive decline—one that names the people who will be responsible for decisions, defines the authority structure, and removes the ambiguity that makes these situations so chaotic when they arrive unplanned.
Longevity is not just a planning consideration. It is the variable that changes every other assumption in the model—and it deserves to be treated accordingly.
10. The philanthropy identity crisis
UHNW families increasingly want their giving to be as strategic and disciplined as their investing. Most are not there yet—and the gap between intention and execution in philanthropy is wider, in my experience, than in almost any other dimension of wealth management.
Donor-advised funds, private foundations, impact investing vehicles, charitable remainder trusts—the tools exist and are genuinely sophisticated. The structures that allow a family to give efficiently, tax-effectively, and with meaningful impact measurement are well-developed. But the intentionality behind many philanthropic efforts remains reactive rather than purposeful. Responding to a gala invitation from someone whose relationship matters. Honoring a longtime business connection with a contribution that was never actually thought through. Writing a cheque because the ask was awkward to decline, and it’s easier to say yes and move on. The result, accumulated over years and decades, is a giving portfolio that is fragmented, emotionally driven, and strategically incoherent.
The irony is stark: these are the same families who would never tolerate that level of fragmentation and drift in their investment portfolio. They would fire an investment manager who couldn’t articulate a coherent strategy. They would demand clarity on objectives, processes, and performance metrics. Yet in philanthropy—which for many of them is the most personally meaningful dimension of their entire financial life—that discipline is consistently absent. I worked with a family that had, over 30 years of giving, contributed to more than 200 different organizations. They could not name the five they cared about most. They could not articulate a theory of change. They had no sense of cumulative impact. When we finally sat down and mapped it together, the experience was somewhere between illuminating and humbling. When a family invests the same discipline in their philanthropy that they apply to their balance sheet—clear objectives, defined impact metrics, intentional vehicle selection, governance across generations—the transformation is remarkable. The giving becomes coherent. It becomes a legacy, rather than a record of transactions. The families who don’t get there risk leaving exactly the wrong thing behind: not poverty, but a legacy of chaos rather than clarity.
The common thread between all 10 worries
Go back to that legal pad on the boardroom table in San Francisco. Ten items, handwritten, from a man who had just completed one of the more extraordinary financial events of his life. Not one of them was about the stock market. Not one was about interest rates, or inflation, or whether technology valuations were stretched. Every single item was about people: his family, his relationships, his legacy, and the structures he did or didn’t have in place to protect what he had spent his life building.
If you read the 10 concerns I have covered carefully, the same pattern emerges in all of them: They are not financial problems. They are family problems with financial consequences—some immediate, some generational. Succession, motivation, governance, legacy: These are deeply human questions dressed up in the language of wealth planning. They require financial sophistication to address properly, but they cannot be solved with financial tools alone. They require candor, trust, relationship depth, and a willingness to have conversations that are awkward and sometimes unwelcome.
The families that navigate this terrain best tend to share one trait: they work with advisors who are willing to raise the uncomfortable questions before a crisis forces them to. Not reactive advisors who arrive after the damage is done with a restructuring plan and a bill. Proactive ones who see the succession gap before it becomes a lawsuit, the concentration risk before the single stock implodes, the governance vacuum before the family fractures, the cyber vulnerability before the wire transfer lands in the wrong account.
That kind of advisory relationship is rarer than it should be. It requires trust built over time, candor that can withstand disagreement, and a genuine commitment to the family’s long-term interests over any short-term convenience. The families worth serving deserve nothing less. And the ones who find it—who build that kind of relationship with a senior advisor who will tell them what they need to hear, not just what they want to hear—tend to be the families whose wealth survives.
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.