Ryan Holiday: Life Is Too Short to Be a Bootlicker

Members of the administration, like Stephen Miller, who spend hours every day kissing Trump’s ass look so pathetic—but since the time of the ancients, courtiers have gone to great lengths to degrade themselves before the vain and vindictive. And one lesson for the ages is to not compromise with an extortionist: it will only lead to more extortion and more pressure because the extortionist wants everything. Meanwhile, Elon’s brain is broken, Peter Thiel spends too much time at dinner parties, Trump’s media diet allows no time for presidential reflection, and authoritarians can be seductive. Plus, Tim sees the redistricting fight looking better for Democrats, and argues that the best way to shut down the talk of a decrepit Trump running in ‘28 is to make sure the Dems win the House in 2026.

Ryan Holiday joins Tim Miller for the weekend pod.

show notes

• Ryan's new book, "Wisdom Takes Work"
• Ryan's book, "Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue"
• Tim and JVL's interview with Ryan about being a dad
• The Daily Stoic Podcast
• Tim's playlist