What’s the point of a $10, $20, $50, or even $100 million legacy if the family doesn’t enjoy or appreciate one another for who they are?
I work with families across the country, always with an educational approach. My goal is to provide value in all aspects of their lives. Naturally, that leads me to integrate into families for everything finance-related, and often beyond.
Many of my clients are first-generation wealth holders. They may have inherited a business that generates significant income, but their parents or grandparents often had minimal liquid wealth. As a result, they have never been taught how to manage a sudden influx of money or the emotional weight that comes with it.
Imagine someone who inherits an aircraft parts business or a large real estate portfolio and later sells it to a strategic buyer or private equity firm. Despite newfound wealth, they often struggle to spend. Why? Because they were raised with values shaped by scarcity, by watching parents stretch every dollar. They know they cannot take it with them, but they also cannot bring themselves to enjoy it.
This inability to spend wisely creates a ripple effect. If they cannot conceptualize spending on themselves, how can they confidently pass wealth to their children? How do they decide who deserves it? How do they make it fair when each child has a different path?
Here’s where the challenge deepens. Many families assess members individually, evaluating them based on their economic value or perceived future potential, without acknowledging the softer, more essential aspects that make a family whole.
There is a common estate planning model that ties access to family wealth to academic achievement. It makes sense on paper. Statistically, higher education correlates with stronger earning potential, so wealth distributions are granted accordingly. When helping clients work through these structures, I often think about how I would build a plan for my own family. At first, it seems simple: tie financial access to education and contribution. But then I think of my sister. I think of my wife. Neither would traditionally be viewed as economic value creators, but their impact is immeasurable.
My wife remembers the small things, like how much someone loves their spouse or how proud they are of their children. People open up to her quickly because she sees them fully. She supports me, my pace, my ambition, and my goals for our family, with unwavering steadiness. That support is the foundation of my professional output.
My sister is fiercely loyal. Protective in a way only an older sister can be. She keeps our family calendar full of birthdays and barbecues and makes sure the traditions stay alive. She is the type who would have buried the kid who bullied me in fifth grade in her backyard, figuratively of course (I think). She is not building economic value, but she is the glue that keeps our family connected. I feel like every family has someone like this in the ranks.
So, how do you account for people like that in a legacy plan? In my experience, most families do not. They overlook the glue, and sometimes even diminish them, because they do not directly generate returns. But here is the truth: without them, there is no legacy.
This brings us to a better framework. You cannot build an enduring estate plan by tying access solely to individual performance or personal milestones. Instead, structure it so that the family, as a collective, needs to achieve a shared level of economic growth or purpose. Treat the family like a business. Create roles. Create purpose. Measure collective outcomes rather than individual ones.
Think of it like this:
• One family member might act as the CEO, full of ambition and ideas for new investments.
• Another might serve as CFO, managing risk and asking hard questions.
• The glue, someone like my wife or sister, becomes the Chief People Officer. They ensure alignment, trust, and continuity.
As a unit, the family sets a return goal, perhaps 7 or 8 percent across the portfolio, and holds one another accountable. If the CEO wants to go big on a high-risk venture, the CFO pressure-tests the numbers, and the glue asks the critical questions: Does this serve our long-term legacy? Does it align with who we are? Maybe the family moves forward, but at a scale that balances ambition with preservation.
This kind of governance structure gives everyone a seat at the table and gives the glue a real, respected voice.
Now, imagine a family full of glue types. No flashy business builders, just emotionally intelligent people who can sniff out bad advisors, build real teams, and create an environment of trust. In many ways, this might be the most resilient family structure of all.
At the end of the day, compounding a legacy does not just happen in markets. It happens at dinner tables. It happens in how you see and value each other, fully.
As I tell my sister: You make sure everyone comes to the table. I will make sure there is always food on it.