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Ryan Holiday - Ego Is The Enemy


Ryan Holiday is an American author, marketer, and entrepreneur. Ryan is an ultra-savvy media strategist, the former Director of Marketing for American Apparel and a media columnist and editor-at-large for the New York Observer. In this fascinating conversation with London Real host Brian Rose, Ryan opens up about the challenges of writing about ego and stoicism, his book creation process and why entrepreneurs should understand that they may be incapable of running what they’ve created.

Growing up in Sacramento, California, Holiday discovered an early passion for literature and philosophy. His fascination with Stoicism, an ancient Greek school of philosophy that emphasises virtue, wisdom, and resilience in the face of challenges, would go on to shape much of his thinking and writing. Holiday found solace and guidance in the works of Stoic philosophers like Seneca, Marcus Aurelius, and Epictetus, and these teachings became the cornerstone of his personal and professional life.

Holiday’s journey into the professional world took an interesting turn when he became the Director of Marketing for American Apparel at the age of 21. His innovative and controversial marketing campaigns garnered attention and set the stage for his future endeavours. Holiday’s strategic approach to media and marketing earned him recognition as a thought leader in the industry. His insights into attention-grabbing tactics and his ability to navigate the ever-changing landscape of digital media have made him a sought-after consultant and speaker.

In 2014, Holiday published “The Obstacle Is the Way,” a book that encapsulates the essence of Stoicism and its application to overcoming challenges. Drawing inspiration from the Stoic concept of turning obstacles into opportunities, the book became an instant success. It resonated not only with business leaders and entrepreneurs but also with a broader audience seeking timeless wisdom in the face of adversity. The book’s popularity catapulted Ryan Holiday into the spotlight as a modern-day philosopher and author.

Continuing his exploration of Stoic philosophy, Holiday released “Ego Is the Enemy” in 2016 which delves into the destructive nature of ego and the importance of humility in personal and professional success. With anecdotes from historical figures and contemporary examples, Holiday skillfully illustrates the pitfalls of unchecked ego and provides a roadmap for cultivating a mindset that fosters growth and resilience.

Ryan Holiday’s impact extends beyond the realms of literature and philosophy; it permeates the worlds of marketing, media strategy, and personal development. Through his exploration and promotion of Stoicism, Holiday has inspired countless individuals to navigate life’s challenges with wisdom, resilience, and a strategic mindset. As an author, strategist, and modern-day philosopher, Ryan Holiday continues to shape conversations, encouraging people to find meaning and purpose in an ever-changing world.


00:00 Trailer.
01:27 Brian’s thoughts on the episode.
04:42 Brian’s Introduction.
05:50 Anyone with ambition needs to be wary of ego and manage that.
07:55 Emulating in his life the greatest fighters as the most humble and stoic people.
09:39 Ryan’s journey from 18 to 26.
11:31 The ego struggles with the conundrum of principle or stubbornness.
13:56 Has writing about ego and stoicism set him up for future scrunity?
14:52 Ryan’s definition of ego.
16:13 What Ryan considered before risking a move to New Orleans to write a book.
18:40 How Ryan sets about writing a book.
21:29 Too young to write a book on stoicism?
23:59 Conscious decisions on different cover styles for ‘Trust Me I’m Lying’ and ‘Obstacle’.
25:00 How Ryan uses his own book launches to advise many other authors.
26:07 Biggest mistake authors make when creating and marketing a book.
28:54 Publication ‘Obstacle’ unexpectedly being taken up by the sports community.
31:23 Decision to return to American Apparel at a time of company change and what it taught him.
34:49 Entrepreneurs have to understand that they may be incapable of running what they’ve created.
35.39 Ego can be a positive, but its negatives can jeopardise that.
36:43 How Ryan realised that he was not getting what he wanted out of life.
37:34 Ryan’s work ethic.
38:48 Adrenalising.
40:06 When we are in the throes of ego we say yes to everything.
41:36 Effects of Fatherhood on the ego and work ethic.
45:38 What his tattoos remind him of.
50:39 Illustrations of non-ego from the past.
52:30 Against the trend advice to not follow your passion.
54:20 Truly successful people compete with themselves.
57:34 Actions speak louder than words.
59:99 In an age of modern technology, why is the book still relevant?
1:01:59 Does Ryan prefer people to read his books or listen to an audio version?
1:03:40 Ryan loves books and has a lot. Reading is an essential human activity.
1:05:15 Ryan’s Texas lifestyle and daily routine.
1:08:51 Strategy to avoid panic attacks and adrenalising.
1:09:53 What is a Fight Club Moment?
1:10:45.Ryan’s concept of rock bottom.
1:12:25 Explanation of chapters in his book headed ‘Maintain sobriety. Entitlement, Control and Paranoia.’
1:14:36 Why finish the book with ‘Always love’?
1:16:28 What Ryan would like people to take away from reading ‘Ego is the Enemy’
1:18:26 Ryan can trace back to his worst moments resulting from his ego.
1:20:29 The art of listening requires taking a step back from your own ego.
1:21:36 Taking Ayauasca not an ego trip.
1:24:16 The next book.
1:24:51 Does stoicism play a part in today’s world?
1:26:31 Why did Marcus Aurelias write a book on stoicism?
1:27:25 Ryan’s take on current politics in the USA.
1:30:09 What does the popularity of Trump in America say about the collective ego of Americans?
1:32:00 Which chapters should Trump read in ‘Ego is the Enemy’?
1:32:42 Success secrets.
1:33:40 Phone call to the 20 year old Ryan Holiday.
1:35:13 Best advice he has ever received.
1:37:04 Advice to the 20 year old who would like to be like him.
1:38:25 How to foster a relationship with a mentor.
1:41:39 Brian’s summing up.


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