Webb Stickney has spent more than four decades working with enterprise-owning families — inside operating companies and inside family offices. In this conversation with Jon Carroll for the Family Office Project, Webb identifies the risks business-owning families most consistently underestimate, and the patterns that separate the families who preserve wealth across generations from those who do not.
Key Takeaways:
Why the operating company rarely appears in a family's risk profile — and why it should
The 80–90% statistic: what drives family business failure by the third generation
The difference between intellectual and emotional readiness for difficult planning conversations
When to begin succession and pre-transaction planning — and why waiting for a transaction to force it is too late
The three-circle model: family, business management, and ownership as distinct roles
How the family office profession has changed over four decades
