The saying “shirtsleeves to shirtsleeves in three generations” encapsulates a common trajectory of family wealth: the first generation builds it, the second enjoys and often depletes it, and the third is left to rebuild from scratch. The underlying causes vary, from poor intergenerational communication to a lack of financial literacy, but the result remains the same—without intentional planning, family wealth tends to dissipate quickly.
David Herritt, head of Truist’s Center for Family Legacy, believes families can break this cycle through strategic engagement and experiential learning. His approach moves beyond traditional estate planning by fostering meaningful connections and financial stewardship across generations.
A New Approach to Family Wealth Planning
The Center for Family Legacy, part of Truist Wealth, employs a novel methodology to help families sustain wealth: gamification. Rather than relying on sporadic financial discussions, Herritt and his team design immersive experiences that encourage collaboration, trust, and financial education in a dynamic setting. These activities range from problem-solving challenges to team-based obstacle courses, shifting wealth conversations from a passive lecture format to an engaging, hands-on experience.
The rationale is simple: traditional wealth planning often takes place in formal office settings, where senior family members dictate decisions while younger generations remain disengaged. Herritt emphasizes the importance of broadening the conversation to include all generations. He refers to this as a “family wealth” mindset—a strategic shift that ensures continuity and shared responsibility in wealth management.
“You can have all the best estate planning structures in place and follow sound investment strategies, but without addressing family dynamics and communication, even the best-laid plans can fail,” says Herritt.
Creating an Engaging and Inclusive Environment
For families to fully embrace wealth stewardship, Herritt advocates for creating what he calls a “joyous” learning environment. His approach acknowledges that financial acumen alone isn't enough—families must also develop trust, mutual understanding, and a shared sense of purpose. This is especially critical for extended families, where cousins or distant relatives may have little day-to-day interaction but will eventually share financial responsibilities.
The team at Truist tailors activities based on each family's unique communication styles, values, and needs. These experiences might include customized trivia games inspired by Jeopardy! or Family Feud, immersive escape room challenges, or even travel-based adventures modeled after The Amazing Race. For younger children, a scavenger hunt that weaves in family history serves as an engaging introduction to legacy and values.
One particularly creative exercise involved a real-life game of Clue. Truist rented rooms in a boutique hotel and divided 50 family members into teams tasked with solving a series of riddles to “save” their kidnapped financial advisor. These challenges required participants to identify key provisions in estate planning documents and review insurance policies, reinforcing financial literacy through an interactive and competitive format.
“These activities ignite competitive energy and bring families together,” says Herritt. “In some cases, families become so engaged that we run out of space. But beneath the fun, there’s a serious objective: strengthening financial acumen and trust.”
Customization and Investment in the Process
The complexity of these activities varies. Some families prefer a light-hearted trivia session about their business, while others engage in multi-day adventures requiring detailed logistical planning. One particularly elaborate Amazing Race-style event took six months to organize and included air travel to bring family members together. To further enhance engagement, Truist has even developed a proprietary board game aptly named “$hirtsleeves to $hirtsleeves.”
Costs are tailored to the scope of services and are billed per meeting in addition to investment management fees. The firm’s approach allows families to customize their engagement level, ensuring that the experience is both meaningful and practical.
Strengthening Family Dynamics Through Wealth Education
These exercises hold particular value for families managing a business or substantial enterprise, where navigating financial decision-making can be especially complex. Beyond financial literacy, these activities help dismantle long-standing biases and interpersonal tensions that often accompany wealth transfers. Discussions about money can be fraught under any circumstances, but when family dynamics are layered in, the challenges multiply. Herritt emphasizes that structured, low-stakes interactions provide a valuable forum for family members to develop effective communication and problem-solving skills.
“It’s about building trust,” says Herritt. “Maybe it’s not that Cousin Joe dislikes me—he just has a very direct communication style. How do I adapt my approach so that we communicate in a healthier, more constructive way?”
These exercises often serve as a foundation for deeper conversations about wealth stewardship, governance, and decision-making. However, Herritt notes that improvement takes time and repetition. Families need ongoing engagement to reinforce these lessons and create a lasting framework for wealth preservation.
“Every family has some level of dysfunction,” Herritt acknowledges. “We’re not therapists, and we don’t conduct counseling sessions. But we do help families navigate the communication challenges that exist in every household.”
A Sustainable Path Forward
For advisors and RIAs working with high-net-worth families, incorporating experiential learning and relationship-building into wealth planning can be a game-changer. Estate plans and investment strategies are essential, but they alone cannot guarantee the longevity of family wealth. By fostering open dialogue, trust, and financial competence across generations, advisors can help families transform their legacy from a fleeting fortune into a lasting institution.
Herritt’s approach offers a compelling model for advisors seeking to deepen client relationships and enhance the impact of their wealth management strategies. When financial education is engaging, personalized, and emotionally resonant, families are more likely to embrace their roles as stewards of wealth—not just for themselves, but for generations to come.
