This conversation aims to put contemporary theories of the brain, and the resulting technological projects related to artificial intelligence and machine learning, into deeper discourse with Hegelian dialectics and logic. The conversation first focuses on introducing the contemporary theory of the brain, founded on the work of Karl Friston's free energy minimisation principle and the ideas of Markov blankets (bounded internal systems). We then situate these theories and models within the context of the difference between external and internal cognition, the importance of boundaries for the maintenance of intelligence processes, the difference in language games between thermodynamics/entropy and ideas of negativity, the unresolvable tension or dialectics of the brain between isolated/seclusion and openness/connection, and finally some speculative hypotheses about the impacts of modern artificial intelligence on the future of human life and society. Throughout the discourse as a whole you will witness the unpacking of a core scientific principle (free energy minimisation) situated in relation to its historical results, and the way in which these results influence our phenomenology and logic.