Piercing questions families often avoid

In today’s episode, I sit down with Ryan Heath, Founder of Trustpoint Legal, to explore what a modern “Family Office 2.0” actually looks like and why the old models are falling short. We talk about how family offices are evolving from static wealth preservation vehicles into operating businesses built around people, purpose, and multi-generational decision making. Ryan shares lessons from working closely with families navigating liquidity events, succession, and generational transitions, and why flexibility and intentional design matter more than rigid structures. The conversation centers on treating the family office as a living organization, not just a collection of legal documents.

Many can relate to putting in strategic plans for their businesses, their health, etc.  What’s funny is we often don’t put the same planning into what’s most important to us - our family.  

Ryan is on a mission to help families change that.

We discuss:

• What defines a Family Office 2.0 and how it differs from traditional family office models

• Why legacy, values, and human dynamics drive long-term outcomes more than tax efficiency

• How flexible mandates help families adapt as generations, priorities, and circumstances change

• The risks of poor communication and rushed planning during liquidity events or succession

• How intentional family meetings and shared mission statements strengthen multi-generational alignment

This episode is especially valuable for founders and families rethinking how to structure wealth, leadership, and legacy in a way that actually works across generations.

Links:

Ryan on LinkedIn - https://www.linkedin.com/in/ryanheath1/

TrustPoint Legal - https://www.trustpointlegal.com/

Topics:

(00:00:00) - Intro
(00:05:11) - Legacy over wealth
(00:09:04) - Flexibility in estate planning
(00:18:25) - The importance of transparency
(00:27:22) - Handling family conflicts
(00:42:00) - Proactive planning and transparency
(00:52:15) - The silver tsunami and trusts for grandchildren
(00:54:28) - Ruling from the grave
(00:57:49) - Trustees and their roles
(01:01:38) - Understanding family offices
(01:06:39) - The three pillars of a family office
(01:09:21) - The complexities of 678 trusts
(01:12:40) - Family limited partnerships explained
(01:15:13) - The importance of succession planning
(01:22:52) - Coordinating family meetings
(01:30:33) - The perfect family office: a case study
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