Ryan Holiday isn’t shy about sharing advice, or, as he describes it, “positive moral instruction.” Through best sellers like The Obstacle Is the Way and Ego Is the Enemy, the author and strategist has built a following from mining history and philosophy for overlooked but time-tested strategies for self-improvement. From Austin, he advises a mostly secret cadre of high-profile NFL coaches, politicians, and athletes, while building his own brand online. With a new book, Conspiracy—which outlines the Hulk Hogan vs. Gawker trial and its not-so-secret backer, billionaire Peter Thiel—as our excuse to have him in, our sprawling interview covers a lot of ground, from collusion to Kanye, Texas politics to our collective resistance to change.
In the second part of our episode is Alejandro Rose-Garcia (who plays music as Shakey Graves), another man who knows a little bit about resistance to change. He can sense there’s already some consternation among his fan base over his just-released album, Can’t Wake Up. The album shifts from angular indie-rock hooks to dreamy atmospherics and back, representing a fairly radical departure from the rootsy Americana-leaning fare that propelled him out of Austin and made him a festival favorite. Earlier this week, he explained to us what’s different, what’s not, and what it means to be a Friday Night Lights alumnus.