Ryan Holiday (@RyanHoliday) is a strategist and writer. He dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, and later served as the director of marketing for American Apparel. His company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written four previous books, including The Obstacle Is the Way, which has been translated into 17 languages and has a cult following among NFL coaches, world-class athletes, TV personalities, political leaders, and others around the world. Ryan lives on a small ranch outside of Austin, Texas, and his latest book is Ego Is The Enemy.
Ryan and I cover a lot in this conversation, including:
- Meltdowns and how Ryan handles them
- Workaholics Anonymous — How it works, what worked for him, what didn’t
- The tipping points for his last book, The Obstacle Is the Way
- External versus internal obstacles
- Sherman versus Grant leadership and “success”
- Howard Hughes versus Elon Musk
- Thinking of “first principles”
If you only have 5 minutes, listen to what Ryan believes is one of the biggest threats to your creativity.
Enjoy!
- Listen to it on iTunes.
- Stream by clicking here.
- Download as an MP3 by right-clicking here and choosing “save as.”
Want to hear another podcast with Ryan Holiday? — In this episode, we discuss the “big three” stoics, how Stoicism applies to the modern world, and how to improve your decision-making when stakes are high (stream below or right-click here to download):
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QUESTION OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.
Scroll below for links and show notes…
Selected Links from the Episode
- Connect with Ryan Holiday:
- Ego Is the Enemy by Ryan Holiday
- The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday
- The Tim Ferriss Podcast, Episode 4: Ryan Holiday
- The Canvas Strategy — What Ben Franklin and Bill Belichick Have in Common
- Our Brand is Crisis
- American Apparel
- Growth Hacker Marketing: A Primer on the Future of PR, Marketing, and Advertising by Ryan Holiday
- Workaholics Anonymous
- How a book on Stoicism became wildly popular at every level of the NFL by Greg Bishop, Sports Illustrated
- Pioneering coach George Raveling’s surprising connection to MLK by Seth Davis, Sports Illustrated
- 1,000 True Fans by Kevin Kelly
- Small Giants: Companies That Choose to Be Great Instead of Big by Bo Burlingham
- Sherman: Soldier, Realist, American by B. H. Liddell Hart
- Billions
- The 4-Hour Workweek by Timothy Ferriss
- Isocrates, Volume I: To Demonicus. To Nicocles. Nicocles or the Cyprians. Panegyricus. To Philip. Archidamus.
- Kanye West’s $53 Million Debt, Explained by Emily Jane Fox, Vanity Fair
- The Spruce Goose
- The Aviator
- Howard Hughes: His Life and Madness by Donald L. Barlett and James B. Steele
- TWA
- Elon Musk Uses This Ancient Critical-thinking Strategy to Outsmart Everybody Else by Drake Baer, Business Insider
- SpaceX
- Knowledge of [Aristotle’s] First Principles
- Tesla Motors
- Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future by Ashlee Vance
- Fahrenheit 451: A Novel by Ray Bradbury
- The Real Reason We Need to Stop Trying to Protect Everyone’s Feelings
- Dilbert by Ryan Holiday, The Observer
- Timeline of Breitbart’s [Shirley] Sherrod Smear by Media Matters
- Gay pastor admits he faked homophobic slur on Whole Foods cake
- Single Dose of Hallucinogen May Create Lasting Personality Change from John’s Hopkins Medicine
- Deep Work: Rules for Focused Success in a Distracted World by Cal Newport
- Dexa Scans
- Coach.me
- Stickk.com
- DietBet
- Real Mind Control: The 21-Day No-Complaint Experiment
- The Five-Minute Journal
Show Notes
- Why I think about Ryan Holiday every morning. [07:30]
- Ryan talks about his tattoos. [08:10]
- Ryan tells us about the hostile takeover of American Apparel and how it forced him to face some hard truths. [10:27]
- The importance of having a ripcord in a contract. [17:32]
- You wouldn’t like Ryan when he’s stressed and chaotic. [19:01]
- At Workaholics Anonymous meetings, they say: “It’s human being, not human doing.” [23:16]
- Ryan talks about how The Obstacle Is the Way was quickly picked up in the world of professional sports. [30:01]
- For Ryan, the selective fame associated with writing for people he respects is preferable to the generalized fame of a household name. [36:50]
- Why does Ryan focus on ego in his latest book? [39:18]
- Ryan explains the way an unchecked ego can distort reality and stunt our ability to learn and improve. [42:57]
- Sherman vs. Grant [45:23]
- “If you start believing in your greatness, it is the death of your creativity.” -Marina Abramović [52:12]
- Just because someone seems successful to you doesn’t mean they’ve accomplished what’s important to them. [56:02]
- The life of Howard Hughes is a cautionary tale. [57:44]
- Just because a megalomaniac asks for your advice doesn’t mean they’re going to process it rationally. [1:01:05]
- Hughes vs. Musk [1:06:48]
- How Elon Musk went to Aristotle’s First Principles at the formation of SpaceX. [1:06:59]
- Why worrying about offending — or being offended easily — stifles creativity. [1:18:07]
- Save the ammo for the right targets. [1:20:39]
- Ryan’s practices and routines for reducing ego. [1:21:45]
- On the importance of social accountability for self-improvement. [1:23:48]
- The no-complaint experiment. [1:26:24]
- Advice Ryan would give to people who want to use the principles from his book in real life. [1:27:50]
- “Keep your identity small.” -Paul Graham [1:32:26]
People Mentioned
- Elon Musk
- Sandra Bullock
- Robert Greene
- Marcus Aurelius
- Dov Charney
- Shane Parrish
- Michael Lombardi
- John Schneider
- Garrett Gilkey
- Shaka Smart
- George Raveling
- Dr. Martin Luther King, Jr.
- Arnold Schwarzenegger
- Chris Sommer
- Eric Weinstein
- Peter Thiel
- Kevin Kelly
- Sigmund Freud
- Bill Walsh
- Cyril Connolly
- Epictetus
- William Tecumseh Sherman
- Ulysses S. Grant
- Napoleon Bonaparte
- B. H. Liddell Hart
- Bernie Madoff
- Marina Abramović
- Brian Koppelman
- Isocrates
- Steve Jobs
- Kanye West
- Howard Hughes
- Richard Nixon
- John DeLorean
- Ferdinand Lewis Alcindor, Jr.
- Aristotle
- Curt Schilling
- Donald Trump
- Ray Bradbury
- Scott Adams
- Shirley Sherrod
- Cal Newport
- Will Bowen
- Plutarch
- Archilochus
- Tony Robbins
- Paul Graham