My First Million Ryan Holiday Reveals How Much Best Selling Authors Make, Crazy Peter Thiel Stories & More
Ryan Holiday is a best-selling author, podcaster, and former marketing director for American Apparel. In a captivating discussion, he reveals the financial landscape of publishing, debunking myths about bestseller lists and exploring the reality of author earnings. Ryan shares intriguing stories about his experiences with high achievers and the importance of authenticity in creativity. Additionally, he dives into the unique journey of reviving a ghost town through digital content, highlighting the power of connection and ambition in unconventional projects.
01:15:45
Wealthy People and Books
- Wealthy people often aspire to write books, demonstrating it's a desirable pursuit.
- A VC who raised $100 million expressed his desire to follow a path similar to author Alain de Botton.
Quality and Quantity
- Ryan Holiday believes quality and quantity in content creation aren't mutually exclusive.
- Bob Dylan exemplifies producing both high-quality and high-quantity work.
Steady Growth
- Ryan Holiday's Obstacle is the Way sold 100,000 copies in its first year and reached 1 million over several years.
- This steady growth contrasts with authors who achieve rapid success, which can be overwhelming.
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Intro
00:00 • 2min
The Economics of Authorship
01:41 • 13min
Exploring Personal Growth Through Podcasts and Philosophy
14:32 • 3min
Balancing Authenticity with Output
17:24 • 11min
Exploring the Challenges of Book Subscription Services
28:32 • 3min
Exploring the Success of Vinyl Subscription Services
32:01 • 2min
Grounded Success and Humility
33:51 • 16min
Reviving Cerro Gordo: A Ghost Town's Digital Renaissance
49:32 • 18min
#417
• Mentioned in 69 episodes
Conspiracy
Ryan Holiday
In 'Conspiracy', Ryan Holiday chronicles the intricate and ambitious plot by Peter Thiel to take down Gawker Media.
The book is based on interviews with key players and delves into the strategic and philosophical underpinnings of Thiel's actions.
It examines the intersection of power, privacy, and free speech in the digital age, highlighting the ruthless and brilliant tactics employed by Thiel.
The narrative transcends a simple tale of a billionaire vs.
a media empire, offering insights into the broader implications for culture and society.
#61
• Mentioned in 233 episodes
The Subtle Art of Not Giving a F*ck
Mark Manson
In this book, Mark Manson argues against the typical self-help advice of constant positivity, instead suggesting that life's struggles give it meaning.
He emphasizes the need to focus on what truly matters and to accept and confront painful truths.
The book is divided into nine chapters and uses blunt honesty and profanity to illustrate its ideas, encouraging readers to find meaning through values they can control and to replace uncontrollable values with more meaningful ones.
#50
• Mentioned in 251 episodes
Moneyball
The Art of Winning an Unfair Game
Michael Lewis
The book tells the story of the Oakland Athletics' 2002 season, where General Manager Billy Beane and his assistant Paul DePodesta used advanced statistical analysis, known as sabermetrics, to assemble a competitive team despite a limited budget.
The approach, pioneered by Bill James, focused on metrics such as on-base percentage and slugging percentage rather than traditional measures like batting average and runs batted in.
This data-driven strategy allowed the Athletics to compete with teams having much larger payrolls, like the New York Yankees, and achieve significant success, including a 20-game winning streak and a playoff appearance.
#133
• Mentioned in 146 episodes
Courage Is Calling
Ryan Holiday
In 'Courage Is Calling', Ryan Holiday explores the virtue of courage through engaging stories about historic and contemporary leaders such as Florence Nightingale, Ulysses S. Grant, Abraham Lincoln, and Dr. Martin Luther King Jr. The book breaks down the elements of fear, cowardice, bravery, and heroism, and shows how to conquer fear and practice courage in daily life.
Holiday also shares personal anecdotes, including his own experiences with courage and cowardice, to emphasize the importance of choosing to act courageously despite the presence of fear.
#4819
• Mentioned in 10 episodes
The Last Lion
Winston Spencer Churchill
William Manchester
This trilogy presents a detailed and revelatory portrait of Winston Churchill.
The volumes cover his life from 1874 to 1965, including his early years ('Visions of Glory, 1874-1932'), his political isolation and warnings about the Nazi threat ('Alone, 1932-1940'), and his leadership during World War II and the post-war period ('Defender of the Realm, 1940-1965').
The final volume was completed by Paul Reid based on Manchester's research and notes after Manchester's death.
#119
• Mentioned in 158 episodes
Mastery
Robert Greene
In 'Mastery', Robert Greene argues that mastery is not an innate talent but a skill that can be developed through a rigorous process.
The book outlines several key stages: finding your life's task, undergoing an ideal apprenticeship, finding the right mentor, acquiring social intelligence, and fusing intuitive with rational thinking.
Greene draws on the lives of historical and contemporary masters such as Mozart, Einstein, and Temple Grandin to illustrate his points.
He emphasizes the importance of deep practice, self-directed learning, and the ability to read and navigate social dynamics.
The book challenges the conventional notion of genius as a genetic gift and offers practical steps for anyone to achieve mastery in their chosen field.
#24
• Mentioned in 344 episodes
The big short
Inside the Doomsday Machine
Michael Lewis
The Big Short tells the story of the 2007-08 financial crisis through the lens of several key players who predicted and profited from the collapse of the housing market.
The book focuses on characters such as Steve Eisman, Mike Burry, Greg Lippmann, and the founders of Cornwall Capital, who saw the impending disaster and made significant gains by shorting the market.
Lewis explains the complex financial instruments and the systemic failures that led to the crisis, making the narrative both accessible and engaging.
#1236
• Mentioned in 32 episodes
The Blind Side
Evolution of a Game
Michael Lewis
The Blind Side: Evolution of a Game is a dual narrative that examines the evolution of offensive football strategy, particularly the rise of the left tackle position, and the personal story of Michael Oher.
The book delves into how the introduction of players like Lawrence Taylor changed the game, emphasizing the importance of the left tackle in protecting the quarterback's 'blind side.
' It also follows Michael Oher's journey from his impoverished upbringing to his adoption by the Tuohy family and his eventual success as a college and professional football player.
The book touches on themes of sport, culture, family, and the complexities of racial and socioeconomic dynamics in American football.
#158
• Mentioned in 135 episodes
The Power Broker
Robert Moses and the Fall of New York
Robert Caro
This book is a monumental biography of Robert Moses, who was the single most powerful man in New York City and State during his time.
It explores how Moses accumulated and wielded power, shaping the city through his public works projects, including highways, bridges, and parks.
The book delves into Moses's early life, his idealistic beginnings, and his transformation into a powerful figure who dominated New York's politics without ever being elected.
It also highlights the social and environmental impacts of his projects and his eventual fall from power.
The biography is renowned for its detailed and nuanced portrayal of power dynamics in urban politics.
#3233
• Mentioned in 14 episodes
Parting the Waters
America in the King years 1954-63
Taylor Branch
Parting the Waters chronicles the struggle for racial equality in America from the twilight of the Eisenhower years through King’s fiery political baptism, the ascension of John F. Kennedy, and the dawning of the New South.
The book covers significant events such as the Montgomery bus boycott, the Freedom Rides, the Birmingham campaign, and the March on Washington for Jobs and Freedom.
It provides a vivid, panoramic portrait of America during this transformative period, highlighting the roles of key figures including Martin Luther King Jr., the Kennedy brothers, and J. Edgar Hoover.
#32
• Mentioned in 306 episodes
The 48 laws of power
Robert Greene
In 'The 48 Laws of Power', Robert Greene and Joost Elffers synthesize three thousand years of the history of power into 48 laws.
These laws are derived from the philosophies of Machiavelli, Sun Tzu, and Carl Von Clausewitz, as well as the lives of influential figures such as Henry Kissinger and P.T.
Barnum.
The book provides tactics, concepts, and lessons on how to achieve and maintain power, emphasizing prudence, confidence, and self-preservation.
Each law is illustrated with historical examples and is designed to help readers understand and navigate the dynamics of power in various aspects of life, including work, social hierarchies, and politics.
#348
• Mentioned in 79 episodes
Titan
The Life of John D. Rockefeller, Sr.
Ron Chernow
This biography by Ron Chernow provides an in-depth look at John D. Rockefeller, Sr., the founder of Standard Oil and one of the most influential figures in American history.
Drawing on unprecedented access to Rockefeller’s private papers, Chernow reconstructs Rockefeller’s troubled origins, his single-minded pursuit of wealth, and his profound religiosity.
The book also delves into Rockefeller’s philanthropic efforts, including his generous donations to the Rockefeller Foundation, the University of Chicago, and Rockefeller University.
Chernow’s narrative synthesizes Rockefeller’s public and private lives, revealing a complex and multifaceted individual who was both a ruthless businessman and a devoted philanthropist.
The book captures a pivotal moment in American history, documenting the post-Civil War shift from small businesses to giant corporations and featuring cameos by notable figures such as Ida Tarbell, Andrew Carnegie, and J.P.
Morgan.
#60
• Mentioned in 235 episodes
Discipline is Destiny
The Power of Self-Control
Ryan Holiday
In 'Discipline is Destiny', Ryan Holiday explores the Stoic virtue of self-discipline, drawing on historical figures and contemporary examples to illustrate its transformative power.
The book emphasizes that discipline is the foundation upon which other virtues such as courage, justice, and wisdom depend.
Holiday argues that self-control is essential for personal triumph and fulfillment, and he provides engaging stories and practical advice on how to cultivate discipline in a world filled with distractions and temptations.
The book also cautions against the perils of extravagance and hedonism, stressing the importance of balance and self-mastery in achieving success and happiness.
#19
• Mentioned in 388 episodes
Good to Great
Why Some Companies Make the Leap... and Others Don't
Jim Collins
In 'Good to Great,' Jim Collins and his research team investigate why some companies achieve long-term greatness while others do not.
The book identifies key concepts such as Level 5 Leadership, the Hedgehog Concept, a Culture of Discipline, and the Flywheel Effect.
These principles are derived from a comprehensive study comparing companies that made the leap to greatness with those that did not.
The research highlights that greatness is not primarily a function of circumstance but rather a result of conscious choice and discipline.
The book provides practical insights and case studies to help businesses and leaders understand and apply these principles to achieve sustained greatness.
#215
• Mentioned in 107 episodes
Liar's poker
Michael Lewis
Liar's Poker is a non-fiction, semi-autobiographical book that details Michael Lewis's three-year tenure at Salomon Brothers, one of Wall Street's premier investment firms in the 1980s.
The book provides a behind-the-scenes look at the culture of bond traders, highlighting the frat-boy camaraderie, killer instincts, and high-stakes games of bluffing and deception.
Lewis describes the creation and use of mortgage bonds, the excessive bonuses, and the ruthless competition among traders.
The narrative also touches on the author's disillusionment with the industry, leading to his resignation and transition into financial journalism.
#375
• Mentioned in 76 episodes
Tools of Titans
The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers
Ryan Holiday
Mike Del Ponte
Therese Plummer
Ray Porter
Tim Ferriss
Kaleo Griffith
Kevin Rose
Jocko Willink
Tim Kreider
Tools of Titans is a comprehensive guide to achieving peak performance and personal transformation.
The book is divided into three main sections: Healthy, Wealthy, and Wise.
It features insights and strategies from over 200 interviews with successful individuals such as Arnold Schwarzenegger, Ariana Huffington, and many others.
Ferriss highlights common patterns among these high achievers, including daily meditation, disciplined routines, and the ability to turn weaknesses into strengths.
The book is designed to be a resource for continuous learning and improvement, providing actionable advice and tools for readers to enhance their health, wealth, and wisdom.
#12
• Mentioned in 444 episodes
The obstacle is the way
Ryan Holiday
In 'The Obstacle Is the Way', Ryan Holiday presents a framework for turning obstacles into successes.
Drawing from the philosophy of Stoicism and the writings of Marcus Aurelius, Holiday outlines three disciplines: perception, action, and will.
He illustrates these principles with historical anecdotes from figures such as John D. Rockefeller, Amelia Earhart, Ulysses S. Grant, and Steve Jobs.
The book emphasizes the importance of perception in shaping one's response to obstacles, the need for intentional and creative action, and the cultivation of will to persist through challenges.
Holiday argues that by adopting these Stoic principles, individuals can transform their obstacles into opportunities for growth and success.
Episode 370: Sam Parr (@TheSamParr) talks to best-selling author, podcaster, bookstore owner, and former marketing director for American Apparel, Ryan Holiday (@RyanHoliday), about how to make money in publishing, creating a masterpiece, and investing in a ghost town.
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Links:
* Trust Me I'm Lying: Confessions of a Media Manipulator
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Show Notes:
(03:55) - Does the bestseller list still matter?
(05:30) - Breaking down the #s of the publishing industry
(29:20) - How big is your team?
(35:10) - Who do you admire?
(44:40) - The pros and cons of reality distortion fields
(50:40) - Ryan's ghost town
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Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more.
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