The cybernetics community owes a great debt of thanks to the editors of Routledge Library Editions: Philosophy of Mind series, for bringing to light a neglected classic of the field in 2015. It was then that their reprint of Kenneth M. Sayre’s Cybernetics and the Philosophy of Mind appeared. Originally published in 1976, Sayre’s book proffers cybernetics as nothing less than a solution to the mind/body problem through a kind of “informational monism” reminiscent of the thought of Gregory Bateson. As such, it provides as fulsomely developed a cybernetic theory as one is likely to find anywhere; one that most certainly deserves a place in the canon of the field’s most substantial works. In my in-depth conversation with Dr. Sayre, now Professor Emeritus of Philosophy at Notre Dame University, we explore the relationship between the “two entropies” of information theory and thermodynamics, parse the notion of feedback into even more fine-grained categories of homeostatic, heterotelic, sentient, and anticipatory, and trace the role of these various types of feedback in processes of evolutionary adaptation, behavioral conditioning and consciousness as well as the development of social structures, language and reasoning leading to the maximization of “negentropic flexibility.” The result is a deeply thought-provoking glimpse of a rigorously argued cybernetic framework deserving of considerable attention within and beyond the field.