I've seen a few of his YouTube IWTYTBR episodes. The ones I've seen have all been with couples, and it came across more like couples' counseling with a financial theme. He emphasized the fact that everyone has a financial history and exposure to family attitudes toward money, not all of which are healthy. People's financial communication styles really can come out of earlier experiences. All the couples did appear to be open to different ways of doing things.
One of his ideas that I think is especially useful is his notion of "guilt free spending". There's a fine line between frugality and cheapness, and between saving and hoarding. How much a person can afford to spend, guilt free, is dependent on the size of the 'stache and the performance of the investments, but the emotional attitude to enjoying a well-earned, affordable luxury is important. How *much* of one's income should be spent may vary depending on income and how far a person is along the FIRE path, and I don't think the show addresses it in as much of a nuanced way as the discussions on this board, but the idea of guilt-free enjoyment is something I held onto.