Some sitters arrive having decided in advance what a photograph is for. Ray Dalio is one of them.
He is a man who has spent decades being listened to carefully, and who has written at length about how thinking should be done. That produces a particular problem for a portraitist, and it is not the one people assume. The difficulty is not reticence. It is fluency. A person accustomed to explaining themselves clearly will keep explaining, and a face that is mid-explanation is a face performing a function rather than occupying itself.