Good mornin’,
There was a relative calm in markets last week and we are seeing them green this morning, taking a breather from the trade-related noise, although there were some important developments. Here at home, we saw another interest rate cut by the Bank of Canada and the appointment of Mark Carney as Canada’s Prime Minister, and it looks like we are in store for a federal election in the coming weeks. Overseas, a partial ceasefire was negotiated between Ukraine and Russia. Meanwhile, some budget changes were approved in Germany that set the stage for a significant increase in military spending and infrastructure investment. Markets and politics aside…….
Who spent their weekend getting ready for tax time!???
Ahhhh good times - yes, it’s tax season. The time of year when inboxes fill with reminders, spreadsheets multiply, and people everywhere are reminded of one of life’s few certainties. As the saying goes—“Nothing is certain except death and taxes.”
Most people attribute that line to Benjamin Franklin, but it actually dates back even further. Still, Franklin gets the credit because he understood the weight of it. Death and taxes are the two inevitabilities we tend to spend our lives avoiding—one because it’s uncomfortable, the other because it’s annoying. But what if we looked at them differently? What if, instead of trying to dodge them, we planned for them with intention?
This is why we consider our Estate Planning with clients such an important aspect of their Wealth planning. Estate planning isn’t just a legal checkbox, but a responsibility. A chance to turn inevitability into clarity. And there’s one tool that stands out in this process—one that most people either misunderstand or overlook entirely: insurance.
The Most Misunderstood Asset Class
Insurance tends to get a bad rap. It’s often seen as a necessary evil—a product sold out of fear. But that’s only one side of the story. Early in my career as a wealth manager, I understood that it was important for me to be able to provide clients the protection and strategies their families deserve. I went through all the excitement of the insurance process to become licensed, qualified to implement insurance strategies, because – there’s another side of insurance, the one that rarely gets told, is that insurance is one of the most powerful, strategic, and flexible asset classes available. It’s not just about death hand taxes—it’s about living intentionally and creating continuity across generations.
Think about it. It’s the only asset class that shows up when it’s needed most—at death. When the estate needs liquidity, when taxes are due, when emotions are high and decisions need to be made. Insurance creates space. It buys time. It allows families to hold onto properties, businesses, and investments instead of being forced to liquidate under pressure. That’s not just protection—that’s planning.
The Rockefellers and the Kennedys
Take the Rockefellers. They didn’t just build wealth—they built a system to sustain it. Through generations, they’ve used insurance and trusts to manage estate taxes and maintain control. The policies weren’t just about covering risks—they were about funding the future. That, combined with family education and governance, is why they remain a symbol of enduring legacy.
The Kennedys, too, understood this game. Joseph Kennedy used life insurance strategically to fund trusts and preserve family wealth. They didn’t see it as a product—they saw it as a pillar. A tool to ensure the estate stayed intact, the taxes got paid, and the legacy carried on.
The Vanderbilts
Now contrast that with the Vanderbilts. Once among the wealthiest families in America, Cornelius Vanderbilt amassed a fortune through railroads and shipping. But without structure, governance, or smart planning—let alone strategic insurance—the wealth evaporated. Within a couple of generations, it was gone. By the nineteen seventies, at a family reunion, there reportedly wasn’t a single millionaire left among them.
Same era. Same level of wealth. One family built systems and used insurance to extend their influence. The other spent freely and left no foundation. It’s a stark reminder: wealth doesn’t sustain itself. Planning does.
The Magical World of Disney
Looking at the ROI (return on investment) benefits of insurance….think of it like buying a GIC with enhanced double-digit returns with the ability to access the cash value or use it strategically as collateral too. Here’s a story people often forget: Walt Disney used the cash value from his life insurance policy to help fund Disneyland when no bank would lend him the money. That’s right—the happiest place on Earth might not exist today if he hadn’t understood how to access capital from within his own system.
Insurance as a Core Allocation
So what does this mean for the rest of us? It means insurance isn’t just a line item. It’s a powerful asset class—one that belongs in the conversation right alongside equities, real estate, and fixed income. Especially for those thinking about intergenerational wealth.
Insurance can be structured to provide tax-advantaged growth, guaranteed payouts, and estate liquidity. It can be used to equalize inheritances, fund charitable legacies, and protect against estate shrinkage. And when paired with trust structures, it becomes a cornerstone of intelligent wealth design.
In other words, it’s not about what insurance costs. It’s about what it unlocks.
Death, Taxes, and Intention
As you continue to prepare everything needed for tax season, give some thought to the fact that there is certainly truth in the fact that – sure - we can’t escape death and taxes….but we can meet them with clarity. We can plan for them with purpose. And we can use misunderstood tools—like insurance—to turn inevitability into intentionality.
Because in the end, the real legacy isn’t just what we leave behind—it’s how well we prepared those who come after us to carry it forward.
Be well and enjoy the moments,
Derek Henderson