How to Preserve Your Family’s Legacy: Why Communication Matters More Than Tax Planning
- Mar 11, 2022
- 5 min read
Updated: Mar 12
The families that lose their wealth across generations almost never lose it because of bad investments or poor tax structures. They lose it because they never learned to communicate about money, responsibility, and shared purpose.
In this episode of The Artisan Podcast, Arthur Salzer, CFA, Founder and CEO of Northland Wealth Management, speaks with Vincent Valeri, MBA, FEA - Family Enterprise Advisor and Legacy Coach, about why intentional communication is the single most important factor in whether family wealth survives, and what families can do to build it.
It Starts With Mindset, Not Frameworks
Valeri’s central argument is that no governance framework, family constitution, or tax plan will work unless the family first makes a conscious, collective decision to communicate. This sounds simple. In practice, it is the step most families skip.
“You can bring in the best communication coach there is. But if the family hasn’t made that conscious decision to say, we want to be a communicating family, a family that believes in trust and effective communication, the rest of the stuff is not sustainable.”
— Vincent Valeri, Family Enterprise Advisor & Legacy Coach
The distinction matters because many families jump directly to structural solutions: trusts, holding companies, shareholder agreements, buy-sell provisions. These are necessary, but they are technical tools that address the “how” of wealth transfer. Without the foundational human work of building trust and communication habits, the technical structures become sources of conflict rather than solutions.
What Happens When Communication Fails: Canadian Examples
The conversation references two of Canada’s most visible family enterprise disputes: the Rogers family and the Stronach family. In both cases, the families had access to the most sophisticated legal and financial advisors available. The structures were in place. What broke down was the human layer: trust between family members, clarity about roles and responsibilities, and the ability to resolve disagreements without litigation.
Valeri points to a broader data point: trust litigation (beneficiaries suing trustees) is now the largest form of litigation in Canada. This represents a systematic failure to prepare beneficiaries for their roles and to build relationships between trustees and beneficiaries before decisions need to be made under stress.
The Wealth Creator’s Hardest Transition: From “Me” to “We”
The qualities that make wealth creators successful, such as laser focus, decisiveness, top-down authority, and a willingness to be right when others are wrong, are precisely the qualities that undermine wealth transition. The mindset that built the wealth is not the mindset that preserves it across generations.
“What’s made most wealth creators very successful has been laser-focused vision. ‘I’m right, you’re wrong.’ Almost like a bull in a china shop. But the transition requires a shift. It’s no longer about me. It has to move to ‘we.’”
— Vincent Valeri
Valeri speaks from personal experience. His father was a wealth creator in Hamilton, Ontario, a first-generation Canadian immigrant who built significant financial success. But when the family business was sold, the family struggled to come together to discuss what the wealth meant, how it should be managed, and what each family member’s role would be. The financial capital was impacted directly because the human capital work had not been done.
How Families Build Intentional Communication
Valeri describes working with families ranging from small, closely held businesses to fourth-generation cousin consortiums with 37+ shareholders. The mechanics vary, but the principles are consistent:
• Monthly family check-ins. Separate from business meetings. One family Valeri works with has five members all working in the business daily. They were losing their family bond because every interaction was about the business. A dedicated two-hour monthly meeting focused exclusively on personal check-ins, not business, has reinvigorated their ability to work together.
• A code of conduct. Before family meetings, establish ground rules: nothing is off the table, participation is required (not optional), what’s said is confidential. This creates the psychological safety that allows difficult conversations to happen.
• Annual family retreats with an educational component. Larger families use retreats as learning experiences: estate plan updates, personal development planning, individual goal-setting and accountability. One family has each member present their personal development accomplishments from the previous year and receive feedback from the group.
• Pre-meeting preparation. Every family member should be individually consulted before group meetings so they feel heard and have contributed to the agenda. Showing up to a meeting where the agenda was set without your input creates disengagement.
Why the Wealth Creator Must Go First
One of Valeri’s most practical insights is about who initiates vulnerability. The patriarch or matriarch has an outsized influence on family culture. When the wealth creator demonstrates vulnerability, admitting uncertainty, asking questions, acknowledging insecurities, it creates permission for everyone else to do the same.
“The most successful and inspiring family meetings I’ve participated in is watching mum and dad, the wealth creators, just be absolutely vulnerable about what they’re feeling. When that family leader goes first and brings that vulnerability to the table, that is what creates safety.”
— Vincent Valeri
This is counterintuitive for wealth creators who have built their identities around competence and control. But in the context of wealth transition, the willingness to say “I don’t have all the answers” is more powerful than any governance structure.
Not All Families Should Stay in Business Together
Valeri is direct about a truth the industry often avoids: not every family should remain in a shared enterprise. Sometimes the healthiest outcome for both the family and the wealth is a structured separation. He cites a family where siblings in the second generation executed an internal transaction, with one brother becoming a larger shareholder, allowing others to pursue independent paths. The family stayed a family precisely because they didn’t force a partnership that wasn’t working.
“We cannot want the family to stay together more than them. Not all families should be together. Pigeonholing siblings or cousins into a partnership that doesn’t work for them as people doesn’t serve the family, doesn’t serve the individual, and won’t serve the money.”
— Vincent Valeri
Recommended Reading for Families
Valeri recommends four books for families beginning this work:
• The Voice of the Rising Generation by James E. Hughes Jr. For rising-generation family members who feel isolated in their experience of inheriting wealth.
• The Cycle of the Gift by James E. Hughes Jr. On the dynamics of giving and receiving wealth across generations.
• Good to Great by Jim Collins. For the concept of Level 5 leadership, which Valeri applies directly to family governance: leading with humility and intentionality rather than command and control.
• In Three Generations by Kristin Keffeler (noted as Kristin Heaney in the podcast). The story of an unknowing inheritor and the frameworks families can use to prepare the next generation.
About the Guest
Vincent Valeri is a Family Enterprise Advisor and Legacy Coach at Vincent Valeri and Associates. Previously, he worked with families at Legacy Capitals, LLC and served as a Wealth Advisor at Scotia McLeod. He holds an MBM from the University of Technology Sydney and a BA in Operational Management from Western Sydney University. Born into a Canadian immigrant family with its own wealth transition experience, Valeri brings both professional expertise and first-person understanding of the human dynamics of family enterprise.
Frequently Asked Questions
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