Matthew Graves is a brilliant thinker who has been a member of the Rationalist movement for a long time. He is an admin at LessWrong, one the most popular Rationality blogs, a former staff writer at the Machine Intelligence Research Institute (MIRI), and has worked as an instructor at the Center for Applied Rationality (CFAR), which hosts retreats and trainings. In this conversation, we talk about most of those things, and also the balance between being on the analytical sidelines of major issues versus being "in the trenches".