Who do I know who has done a wealth transition well and what would I ask them if I had the courage?

Most founders know one or two peers who have actually done this well. The challenge isn't finding them. It's being willing to admit you need to ask. Successful transitions are quiet. The founders who pulled them off don't talk about the messy years at investor events. They will tell you privately, in confidence, what really happened. Kris Kluver opens The Dysfunctional Family Office with this exact moment. A banker named Brian asks his most successful client, Ben Christoff, how he managed it. The conversation that follows is what changes everything. The questions you'd want to ask are usually about the parts you're most afraid to admit you don't know. The pride is the only thing standing between you and the answer.