What does it mean for an advisor to be willing to get fired?

It means showing up to every meeting prepared to say the hard truth, even if it costs the relationship. Kris Kluver, in The Dysfunctional Family Office, has Ryan describe this as his working principle. If he's not willing to call out the founder's blind spots in real time, he's not the right person for the work. Most advisors avoid the hard conversation because losing the client is expensive. The result is a family of advisors who quietly agree with whatever the founder wants and produce a transition plan that misses the point. The right advisor sits in the discomfort. They tell you the thing your team won't tell you. They risk the relationship to serve the actual outcome. The single best test of a founder advisor is whether they show up that way every time.