220 Doing Legacy Better: The Conversation Advisors Aren’t Having (and Why It Wins Trust + Retention) with Alex Kirby
Episode Description
In this episode, Sten Morgan sits down with Alex Kirby, founder of Total Family, the company behind FamilyOS, a legacy platform built for wealth advisors. Total Family helps advisors support families in defining Values, Purpose, and Roles, and preserving stories and legacy so families can pass on more than wealth across generations.
They unpack why legacy work is both a massive differentiator and a low-risk conversation starter for prospects and clients—especially business owners and high-net-worth families who rarely have a place to talk about meaning, values, purpose, and family dynamics.
Alex shares his personal story—growing up as an only child with 10 step/half siblings through six marriages and five divorces—and how working with closely held businesses taught him that money doesn’t solve family complexity. That realization led him into legacy frameworks (Hughes, Grubman, York) and eventually into building software that makes legacy practical and scalable.
Sten explores how legacy conversations can drive new business, retention, and multi-generational stickiness, and how Total Family’s “client-does-the-work, advisor-debriefs-the-output” approach reduces the time burden while deepening trust.
Takeaways
Legacy ≠ estate planning. Estate planning is the structure—legacy is the “why.”
Alex compares estate planning to building a house: documents are the blueprint + construction, but legacy is the earlier step—standing on the land asking, “What do we want this to become?”
“Wealth” is bigger than money: it’s the well-being of the family.
Total Family focuses on values, purpose, legacy letters, family histories, and identity—not asset allocation—because advisors already handle the financial mechanics.
Legacy is a differentiator because the bar is lower than advisors think.
Competing on market commentary is brutal (everyone plays there). But in legacy, clients have few outlets—so asking thoughtful questions alone can set you apart.
You don’t need all the answers—just ask better questions and follow up well.
A simple prompt like, “When I say legacy, what comes to mind?” can open a door clients often walk right through.
Clients aren’t uninformed about estate planning—they’re uninspired.
Alex cites David York (Entrusted): people know they need documents, but they don’t feel the meaning behind them. Facilitate the “why,” and the follow-through becomes natural.
Legacy work is retention—but the real retention problem is the spouse and kids.
Advisory retention might be ~97% while the original client is alive, but it can drop dramatically when assets transfer. Legacy work builds real relationships before that moment.
Advisors must decide what categories they won’t budge on—and legacy may belong on that list.
Sten notes some planning topics are non-negotiable. Alex agrees in principle, but emphasizes legacy can start with “small steps” rather than a heavy emotional leap.
Make legacy accessible: prompts matter.
Asking a stoic patriarch to “write a love letter” may shut things down—but asking for a paragraph on hard work, responsibility, friendships, or what shaped them can unlock the same depth through a different door.
Scale requires this rule: clients do the work; advisors integrate and debrief.
Total Family’s design helps clients define values/purpose in minutes, then the advisor has a simple high-impact role: review outputs, ask meaning questions, and connect it back to planning.
Lead by example or clients will feel the disconnect.
Alex strongly recommends advisors go through the tool themselves first. When you’ve wrestled with your own values/purpose, you show up with authenticity—not a scripted “legacy pitch.”