Ryan Holiday, bestselling author and modern interpreter of Stoic philosophy, joins Governor Gavin Newsom at the California Governor's mansion in Sacramento. Holiday, originally from Fair Oaks, California, dropped out of UC Riverside at 19 to work as research assistant for Robert Greene, author of The 48 Laws of Power.

The conversation explores Holiday's journey from aspiring heavy metal musician to philosophy writer, his time at American Apparel during its spectacular rise and fall, and his discovery of Stoicism through Meditations by Marcus Aurelius. They discuss how ancient philosophy applies to modern challenges, from media manipulation to political leadership.

Holiday reflects on his prescient 2012 book Trust Me, I'm Lying, which predicted many current media problems, and explains how Stoic principles like 'the obstacle is the way' from The Obstacle Is the Way can guide personal and political action. The discussion touches on responsibility, agency, and the need for philosophical grounding in turbulent times.

From Sacramento Suburbs to Robert Greene's Apprenticeship

Holiday grew up in Fair Oaks, California, with a police detective father and school principal mother, wanting to be in a heavy metal band until discovering writing in college.

At UC Riverside, he wrote about Robert Greene, author of The 48 Laws of Power, and became his research assistant at age 19, dropping out of college for what he called an apprenticeship.

Greene's Mastery became Holiday's template for understanding how to become great at something - first find what lights you up, then attach yourself to someone who has done it.

The 48 Laws of Power is 'consistently one of the most shoplifted books in the country' and 'banned in most prisons' - the Innocence Project tells people not to have it in their cells as it will be used against them in sentencing.

American Apparel's Rise and Fall as Ego Lesson

Greene got Holiday a marketing job at American Apparel, where at 22 he was running marketing for a publicly traded company - 'I had no business being there.'

The company was 'at one point the largest garment manufacturer in the Northern Hemisphere' but 'destroyed itself' through the founder's genius becoming 'demonic energy.'

Reading Budd Schulberg's The Harder They Fall provided Holiday's breakthrough moment about leaving, with its insight that 'you cannot deal in filth without becoming the thing you touch.'

Holiday wrote Ego Is the Enemy as American Apparel imploded, having a 'ringside seat' to how 'that line between genius and madness is very fluid.'

Discovering Stoicism Through Marcus Aurelius

Doctor Drew introduced Holiday to Stoicism in 2006 at a conference sponsored by Trojan Condoms, recommending Epictetus and Marcus Aurelius.

Meditations struck Holiday as 'the private thoughts of the Emperor of Rome' talking to himself about 'how to not just be a productive person and a strong person, but also a wise person and a good person.'

During the 2020 pandemic, Holiday realized Meditations was written during the Antonine plague - 'this fifteen year pandemic that killed millions' - making it fundamentally a plague book.

Marcus Aurelius wrote about 'two types of plagues: one that can destroy your health and one that can destroy your character' - Holiday watched people get radicalized during COVID-19.

Media Manipulation and Truth in the Digital Age

Trust Me, I'm Lying, written in 2012, exposed how 'the economics shape' media and how easy it is to 'inject things into that slipstream' - predicting manipulation tactics a decade early.

Holiday demonstrates the media cycle: 'Daily Mail says something, The California Post says something. Now The New York Post says two sources have confirmed something' - creating false validation.

Trump intuitively understands this system, using phrases like 'a lot of people are saying' so 'things that are not true become true by you bump into them enough times.'

The Naval Academy canceled Holiday's lecture an hour before he was scheduled to speak for planning to criticize book banning, proving that 'canceling the lecture an hour before I'm supposed to go on is going to add a lot more attention.'

The Obstacle Is the Way: From Professional to Personal

The Obstacle Is the Way popularized Marcus Aurelius's principle that 'what stands in the way becomes the way' - initially Holiday interpreted this as dealing with professional obstacles.

Holiday later understood the fuller meaning: when people 'cause problems for us, they can get in our way, but we always have the ability to accommodate and adapt' - it's about growing as a person through difficult relationships.

The Stoic version of optimism isn't 'this is going to go amazingly' but 'I'm going to be better for this, however horrible it is' - like Admiral Stockdale's approach to surviving seven years as a POW.

Stockdale learned Stoicism at Stanford in 1961, and 'the reason that Stockdale doesn't break is that he is introduced to these things at a woke liberal institution run by California hippies.'

Stoicism's Influence on American Democracy

The founding fathers were heavily influenced by Stoics - 'Jefferson as Jefferson as Seneca in French on his nightstand when he dies' and they were 'masquerading as these Roman characters' in the Federalist Papers.

Victor Frankl believed the Statue of Liberty should be 'counterbalanced by a statue of responsibility in San Francisco Harbor' - Holiday and Senator Padilla are discussing making this real.

John Adams said that without virtue in the people, 'the constitution cannot' hold - 'it will go like a whale through a net' because freedom must be counterbalanced by responsibility.

The Stoic teaching about 'circles of concern' means 'pulling these outer rings inwards' - expanding our sense of obligation from immediate family to all humanity.