The Next-Gen Wealth Transfer Problem: the Family Office Struggle

Over the next quarter-century, next generational wealth transfer will reach record-breaking figures. America in particular stands at the edge of a historic shift in personal finance, with a generational transfer of nearly $124 trillion in assets over just 25 years. According to a wealth transfer report from Boston wealth management firm Cerulli Associates, published in June 2025, a combination of demographic and economic forces will see a record amount of wealth move from baby boomers and older Americans to heirs, widows, and charities by 2048. Yet size is not the industry's real challenge. The harder problem is continuity — and nowhere is that more acute than in family-owned businesses, where the money and the enterprise must transfer together.

The numbers here are sobering. 70% of family wealth is lost by the third generation, according to research from The Williams Group. Governance structures often lag behind ambition: more than 60% of families say preparing the next generation is a top priority, yet most family offices lack formal programmes to do so, and 38% see maintaining unity and preserving the legacy as a major challenge, with nearly three-quarters having no succession plan. Meanwhile, a perception gap is widening between generations. Deloitte Private's research found that when asked whether their family business could withstand the departure of an important family employee, 24% of the current generation strongly agreed their succession plan would allow the business to continue running smoothly, while only 13% of next-generation respondents felt the same.

Multi-generational retreats can help build family cohesion around matters of legacy, ethics, and identity.

This is precisely why forward-thinking family offices are turning to a blended format: part corporate retreat, part family holiday. As one strategist puts it, "creating mentorship programmes, facilitating family retreats, or designing next-gen investment education delivers more than a service, it delivers continuity", helping to build "relationships that last across generations". Advisers to family enterprises increasingly recognise that setting up multi-generational retreats using outside facilitators with expertise in family or group dynamics can help build family cohesion around matters of legacy, ethics, and identity, while preparing younger members for the people-management aspects of their future oversight roles. Crucially, emotional readiness is as important as financial knowledge when navigating a change in leadership.

More than 60% of family offices prioritise preparing the next generation, but most lack formal programmes to do so.

The most effective format is neither a boardroom nor a beach — it is both. Structured travel that combines governance sessions, mentoring and strategic dialogue with genuine shared experience gives rising generations a low-stakes environment in which to build the trust that formal meetings rarely produce. A one-to-three-day offsite at a conference hotel, private club room or boutique retreat centre reduces daily distractions, allowing facilitators to combine case studies, role-plays and hands-on sessions such as family meeting simulations, while still leaving room for the kind of unstructured, informal connection that only travel affords.

Structured travel that combines strategic workshops with genuine shared experience gives rising generations a low-stakes environment in which to build trust.

For families whose wealth is tied to an enterprise, journeys designed this way do double duty: they build the technical fluency the next generation needs to lead, and the relational fabric that keeps them willing to. At Revamont, we design precisely these hybrid experiences — where the agenda includes both the strategy session and the shared table — so that businesses, and the families behind them, endure well beyond the next handover.

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