I *am* surprised by this given O'Leary's approach to personal finance as described in his Cold Hard Truth books. I mean, while he can certainly afford it, he certainly could get his hair cut for a lot less. While he explains the frequency and the reason for wanting his hair kept at that level of grooming, I don't get why he pays more for the cuts. I wonder if he is just being a generous tipper, valuing the service he is getting from the hair-cutters? That would make it less "shameful" from my perspective than simply paying more for the haircut in the first instance. But, really, the more I think about it, the less shameful it seems for him to "overpay" (by overpay, I mean pay more than the average market price) for a service he values. I suspect he also enjoys the personal interactions with the people who do his hair and other grooming.