After more than 26 years of producing legacy films for families and family businesses, I’ve had the rare privilege of sitting with individuals who have built extraordinary lives—financially, professionally, and personally. Many of them are founders, philanthropists, investors, and matriarchs and patriarchs whose decisions shaped not only their families, but institutions and communities.
When people reflect on their lives at this level, the conversation rarely centers on wealth itself. Instead, it turns to meaning: how values were formed, how pivotal decisions were made, and what they hope future generations will understand—not just about success, but about character, and about creating a satisfying and fulfilling life.
What stands out most to me is not only what families are proud they preserved, but what they wish they had captured.
What Families Never Regret Preserving
Families never regret taking the time to preserve:
- The stories behind major financial, business, and life decisions
- The values that guided those decisions—especially during difficult or uncertain moments
- Personal histories that explain why things were done a certain way, not just what was done
- The voice, presence, humor, and perspective of family leaders
These are not things found in estate plans, trust documents, or investment summaries. Yet they are often the very elements that determine whether future generations steward wealth with wisdom—or struggle to understand the responsibility they inherit.
The Regrets I Hear Most Often
Across generations and across net worth levels, I hear remarkably similar reflections:
- “I didn’t realize how much context would be lost.”
- “I assumed the next generation understood how we got here.”
- “I thought we would have more time to talk about this.”
- “ I wish I had done that for my parents.”
- “ I wish I could ask my mom more questions, but now it’s too late.”
- “ I wish I had filmed the story of how my grandparents started the business.”
For families with significant wealth, these gaps can be particularly costly—not financially, but relationally. When values and intent are not clearly articulated, misunderstandings grow. Family dynamics become strained. The human capital of the family is left unsupported.
Why Film Is Different
A professionally produced legacy film does more than document a life story. It captures nuance—tone, emotion, reflection, and lived experience—that written records simply cannot.
For future generations, seeing and hearing a parent or grandparent explain their thinking in their own words creates understanding that is deeply human. For families today, the process itself often opens meaningful conversations across generations—sometimes for the first time.
This is why family offices increasingly view legacy films not as keepsakes, but as strategic tools that support continuity, governance, and shared values.
A Resource for the Living, Not Just the Future
Many families initially approach a legacy film as something meant for children and grandchildren decades from now. What often surprises them is how impactful the experience is in the present.
We regularly see families use these films to:
- Anchor family meetings and retreats
- Support next-generation education
- Onboard new family members
- Provide context during transitions of leadership or liquidity events
- Strengthen connection across branches of a growing family
In this way, legacy films become living assets—used, referenced, and revisited over time.
A Thoughtful, Discreet Process
At Family Legacies, we work closely with families and their advisors to ensure the process is handled with discretion, care, and respect for privacy. We film in clients’ homes or offices, creating a comfortable environment that encourages authenticity. Every project is custom-designed, reflecting the family’s culture, complexity, and long-term goals.
After producing more than 250 legacy films, one thing has become clear: the families who move forward never regret it. The only regret I hear is waiting until it’s too late.
A Final Thought
Wealth can be transferred efficiently. Wisdom cannot—unless it is intentionally preserved.
For families and family offices focused on sustaining not just financial capital, but human and intellectual capital across generations, legacy films offer something uniquely powerful: clarity, continuity, and connection.
If this is a conversation your family or the families you serve are beginning to have, I welcome the opportunity to explore whether this work might be a meaningful fit.
