Why does my advisor sharing his own family struggles matter for our work?

Because lived experience produces a kind of credibility credentials don't. Kris Kluver, in The Dysfunctional Family Office, has Ryan tell the Mitchells directly. He didn't get into this work from a textbook. He got into it because he watched his dad's side of the family blow through everything they inherited. Multiple generations of wealth, gone. Not because of bad investments. Because the family couldn't talk to each other and resentments festered. Advisors with skin in the game work differently. They've sat with the consequences. They know what's at stake. They can hold the room when it gets hard because they've been in the room when it got hard. UHNW families generally don't trust an advisor who hasn't lived something hard. They shouldn't.