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Ryan Holiday

Ryan Holiday is an American writer and media strategist whose career spans provocative marketing campaigns and popular works on Stoic philosophy. After dropping out of college at age 19 to apprentice under author Robert Greene, Holiday served as director of marketing for American Apparel, where he orchestrated viral strategies amid the company's controversial advertising. He later founded the advertising agency Brass Check, consulting for clients including Google and TASER. Holiday's authorship gained traction with Trust Me, I'm Lying (2012), an exposé on media manipulation drawn from his industry experience, followed by Stoicism-infused bestsellers like The Obstacle Is the Way (2014), Ego Is the Enemy (2016), and Stillness Is the Key (2019), which have influenced athletes, executives, and leaders across professional leagues such as the NFL, MLB, and NBA. These volumes, totaling over a dozen titles on philosophy, history, and self-mastery, emphasize timeless virtues amid contemporary challenges, with adaptations including daily devotionals and paternal advice in The Daily Dad (2023). Through his platform The Daily Stoic, Holiday disseminates practical interpretations of ancient texts, prioritizing empirical resilience over fleeting trends.

Biography

Early life and education

Ryan Holiday was born on June 16, 1987, in . His father worked as a , and his mother served as a high principal, providing a stable, conventional family environment during his upbringing. Holiday completed his but has not publicly detailed specific high schools attended, with his mother's role in education likely influencing early exposure to academic settings. He enrolled in college at the , pursuing higher education amid growing interests in writing and media. At age 19, Holiday dropped out of college to apprentice under author , prioritizing practical experience in writing and strategy over formal degree completion. This decision marked an early rejection of traditional academic paths in favor of self-directed learning and professional immersion.

Marketing career beginnings

Holiday dropped out of the , at age 19 to apprentice under , author of , marking the start of his professional involvement in marketing and strategy. This apprenticeship provided early exposure to power dynamics and promotional tactics, which Holiday later applied in client work. At age 20, Holiday relocated to to collaborate with author on book marketing, including campaigns for I Hope They Serve Beer in Hell, which had received a $7,500 advance from a small publisher. He contributed to stunts such as a 2009 Planned Parenthood-related provocation that generated week-long media coverage, honing techniques in viral promotion and media engagement. These efforts helped elevate Max's profile through targeted online strategies and publicity maneuvers. Holiday then joined as of marketing, a role he held for several years starting around 2006, where he directed provocative advertising and PR campaigns amid the company's controversial image under founder . In this position, he executed media pranks and growth-hacking tactics to drive traffic and sales for the apparel retailer, including fabricated stories that infiltrated outlets like and . These early experiences emphasized exploiting blog and ecosystems for amplification, as Holiday later chronicled in his writings on industry practices.

Transition to authorship and Stoicism

Holiday first encountered during his undergraduate studies at the , around age 18, where he focused on ancient and found its emphasis on and self-mastery compelling. Although he dropped out to pursue a career in , Holiday later credited Stoic principles with aiding his professional success in and growth strategies, applying concepts like perceiving obstacles as opportunities during high-pressure campaigns for clients such as . Following the 2012 publication of his confessional marketing exposé , which detailed his tactics for generating and provoked backlash, Holiday experienced a period of that prompted a deliberate return to . In early 2012, he articulated a shift toward self-criticism and accountability, recognizing that demanded confronting personal faults rather than external blame, marking a pivot from cynical strategies to ethical self-improvement. This culminated in his authorship of , published on May 1, 2014, which adapted ideas—primarily from Marcus Aurelius's —into a framework for transforming adversity into advantage, drawing on historical examples to illustrate perception, action, and will as tools for triumph. The book's release represented Holiday's full transition to Stoic-themed writing, blending his marketing acumen with philosophical advocacy to reach broader audiences seeking practical wisdom amid modern challenges; it sold over a million copies and influenced figures in , , and by emphasizing 's utility for and mental fortitude over abstract theory. Subsequent works like (2016) and (2016) solidified this direction, establishing Holiday as a popularizer of through accessible, action-oriented interpretations rather than academic .

Philosophical Contributions

Core Stoic principles advocated

Holiday prominently advocates the Stoic dichotomy of control, a foundational principle originating from Epictetus that distinguishes between what is within one's power—such as judgments, intentions, and actions—and what is not, including external events and others' opinions. He teaches that focusing energy solely on internals fosters resilience and reduces unnecessary suffering, as exemplified in his instruction to "only focus on what's in your control" amid life's uncertainties. Another key tenet Holiday promotes is , or the love of fate, which encourages not merely accepting but embracing all circumstances as opportunities for growth and virtue. Drawing from Nietzsche's interpretation of ideas alongside ancient sources, he argues this mindset transforms adversity into fuel for excellence, stating that " is Stoicism's formula for human greatness" by viewing every event as a chance to practice self-mastery. Holiday consistently highlights the four cardinal virtues—wisdom (), courage (), temperance (), and justice ()—as the core of Stoic ethics and the path to , or flourishing. In works like Right Thing, Right Now (2024), he positions as foundational, requiring and discipline to act rightly regardless of personal cost, while involves deliberate reflection to align choices with these virtues. He integrates these into daily practice, asserting that true manifests through virtuous behavior rather than mere intellectual assent. Additional principles include premeditatio malorum, or premeditation of evils, to avoid suffering imagined troubles by mentally rehearsing potential hardships, and treating success and failure indifferently to maintain . Holiday frames these as practical tools for turning obstacles into advantages, as detailed in (2014), where perception, action, and will form a framework for perceiving challenges accurately, acting persistently, and accepting outcomes with resolve.

Applications to modern life and leadership

Holiday's application of Stoicism to modern life centers on reframing adversity through disciplined perception, persistent action, and acceptance of what cannot be controlled, principles derived from ancient texts like Marcus Aurelius's . In (2014), he articulates a three-part framework—perception (viewing challenges objectively), action (iterative effort without attachment to outcomes), and will (enduring hardship with resolve)—to transform setbacks into advantages, citing historical examples such as Thomas Edison's iterative failures leading to the light bulb's invention on October 21, 1879. This method has practical utility in daily routines, encouraging individuals to dissect problems into manageable components rather than succumbing to frustration, thereby fostering resilience amid economic uncertainties or personal disruptions like job loss. In leadership contexts, Holiday warns that undermines effective by inflating self-importance and distorting reality, advocating instead for as a safeguard against complacency and error. (2016) examines ego's detrimental phases—aspiration (where it stifles learning), success (where it breeds arrogance), and failure (where it fuels denial)—using cases like General George McClellan's overconfidence during the U.S. Civil War, which delayed Union advances in 1862. Leaders applying this include executives who prioritize team input over personal acclaim, reducing risks of strategic missteps in competitive markets; Holiday substantiates this with evidence that ego-driven figures, such as disgraced financier , ignored warning signs leading to his 2008 collapse. Holiday extends Stoic wisdom to leadership through stillness, defined as intentional pauses for clarity amid chaos, essential for high-stakes environments like corporate boardrooms or . In Stillness Is the Key (2019), he draws on figures such as President , who maintained composure during the 1962 by retreating to quiet reflection, and General , whose deliberate solitude informed D-Day planning on June 6, 1944, to argue that such practices enhance focus and ethical judgment. For everyday application, he recommends routines like scheduled non-negotiable downtime or nature immersion to counteract digital distractions, enabling leaders to discern signal from noise in data-overloaded decisions; this counters the hyperactivity glorified in modern productivity culture, which Holiday critiques as counterproductive based on historical precedents of overextended empires collapsing from internal exhaustion.

Writings and Media

Major books and themes

Holiday's early works focused on media and marketing strategies, drawing from his professional experience. In Trust Me, I'm Lying: Confessions of a Media Manipulator (2012), he details tactics for exploiting online news cycles, such as fabricating stories to propagate through blogs and traditional outlets for client publicity, arguing that the incentives of digital media prioritize speed over verification, leading to widespread misinformation. Growth Hacker Marketing: A Primer on the Future of PR, Marketing, and Advertising (2014) outlines low-cost, data-driven methods for rapid user acquisition and product scaling, exemplified by techniques used by companies like Dropbox and Airbnb to achieve exponential growth without traditional advertising budgets. Perennial Seller: The Art of Making and Marketing Work That Lasts (2017) examines principles for creating timeless content and products, emphasizing quality, positioning, and sustained promotion over fleeting trends, with case studies from authors, musicians, and filmmakers who achieved enduring success. Transitioning to Stoicism, Holiday's books adapt ancient philosophy for contemporary challenges, often structuring arguments around historical examples and practical exercises. The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph (2014) posits that adversity can be reframed through three disciplines—perception (controlling one's view of events), action (persistent effort despite setbacks), and will (accepting what cannot be changed)—illustrating with figures like Thomas Edison and John D. Rockefeller to demonstrate how obstacles foster resilience and innovation. This forms the first of a thematic trilogy, followed by Ego Is the Enemy (2016), which contends that unchecked ego undermines aspiration, success, and recovery by fostering delusion and entitlement; Holiday advocates humility and self-awareness as antidotes, citing failures of leaders like General George McClellan alongside successes of those who subordinated self to duty. Completing the trilogy, Stillness Is the Key (2019) promotes cultivating inner calm amid external chaos as essential for clarity, creativity, and endurance, drawing on practices from Stoics, monks, and modern figures like John Lennon and Fred Rogers to argue that stillness enables better decision-making and performance. Holiday's Stoic output expanded with (2016), a year-long guide pairing quotes from philosophers like and with Holiday's commentary on applying their insights to daily obstacles such as anger, fear, and ambition. Lives of the Stoics: The Art of Living from to (2020), co-authored with Stephen Hanselman, profiles ten Stoic thinkers, highlighting their personal struggles and virtues to humanize the beyond abstract principles. A virtues series followed: (2021) frames as proactive bravery in facing fear, using anecdotes from to ; Discipline Is Destiny: The Power of (2022) underscores and routine as paths to mastery, contrasting indulgent failures with disciplined triumphs like those of ; and Right Thing, Right Now: Good Values. Good Character. Good Deeds. (2024) explores and moral action, advocating restitution and integrity through examples like Abraham Lincoln's . These works collectively emphasize Stoic tenets—virtue as the sole good, rational response to externals, and preparation for hardship—as empirically grounded tools for personal and professional efficacy, often validated by Holiday's analysis of historical outcomes rather than untested ideals.

Daily Stoic platform and extensions

The Daily Stoic platform, launched by Ryan Holiday in 2016 as a digital extension of his book of the same name, operates through the website dailystoic.com to deliver practical Stoic teachings via articles, quotes, and reflections tailored for modern challenges. Its foundational element is a free daily email newsletter, which reaches over 300,000 subscribers and pairs ancient Stoic excerpts—primarily from philosophers like Marcus Aurelius, Seneca, and Epictetus—with Holiday's concise analysis and exercises for immediate application. The platform further includes The Daily Stoic Podcast, a weekday audio series hosted by Holiday that repurposes newsletter content into narrated meditations while incorporating extended discussions and guest interviews on , , and decision-making. Extensions encompass Daily Stoic Life, a subscription-based membership providing exclusive content such as advanced series, a private for peer discussions, and downloadable resources like ebooks on Stoic routines. The affiliated store at store.dailystoic.com offers structured programs, including the 9-week Wealthy Stoic course on cultivating and contentment via habits, the Leadership Challenge with video sessions modeling historical figures like , and seasonal initiatives such as the New Year, New You challenge featuring Q&A recordings and habit-building prompts. Additional -driven challenges target specific domains, like Read to Lead for enhancing reading discipline or The Stoic Parent for applying to family dynamics. These components collectively form a ecosystem that amplifies accessibility, with paid extensions funding deeper engagement through accountability and specialized training, while maintaining the platform's emphasis on empirical self-improvement over abstract theory.

Business and Lifestyle Ventures

Marketing agency and strategies

Holiday co-founded Brass Check, a and , in by merging his efforts with those of a former business partner. The firm specializes in creative advisory services for authors, media companies, startups, book publishing, , product launches, and social/ strategies. Brass Check has served clients such as Google, TASER, Complex, and bestselling authors including Neil Strauss, Tony Robbins, and Tim Ferriss. In one instance, the agency achieved five simultaneous placements on the New York Times Bestseller list for its author clients. The agency's strategies prioritize growth hacking over traditional advertising budgets, emphasizing data-driven experimentation, viral dissemination through media channels, and non-conventional PR tactics to amplify reach with minimal expenditure. These approaches, informed by Holiday's prior role at American Apparel, focus on leveraging controversy, user-generated content, and targeted influencer engagement to drive sales and visibility, as applied to book launches and product promotions. For example, Brass Check has supported multi-platinum musicians and tech firms by integrating email funnels with social proof mechanisms to convert audiences efficiently.

Texas ranch and Painted Porch bookstore

In 2015, Ryan Holiday and his family relocated to a 40-acre in , outside Austin, where he conducts much of his writing and professional work alongside hands-on ranching activities. The property supports livestock including , donkeys, and goats, reflecting Holiday's emphasis on self-sufficient, deliberate living informed by principles of resilience and productive labor. In Bastrop proper, Holiday co-owns and operates The Painted Porch Bookshop with his wife, Samantha Holiday, an established in 2021 at 912 Main Street in the historic area. The venture originated from an idea in fall 2019 but faced delays due to the , with construction beginning in March 2020 and the opening occurring amid ongoing restrictions, which Holiday later described as a test of Stoic endurance against uncertainty. The shop curates titles focused on , history, and self-improvement, aligning with Holiday's authorial themes, and extends services like nationwide shipping and regular storytime events on Thursdays and Saturdays at 10:30 a.m. Beyond retail, functions as a multifunctional space for Holiday's operations, serving as an for employees, a venue for recording podcasts and producing content, and incorporating elements from , such as a tree felled during the 2021 Texas freeze integrated into the mezzanine design. It operates through from 10 a.m. to 7 p.m. and extends to 8 p.m. on Fridays and Saturdays, contributing to the local economy while supporting Holiday's broader mission of promoting accessible philosophical resources.

Personal Life

Family and relationships

Ryan Holiday has been married to Samantha Marie Hoover since February 27, 2015, when the couple wed at the Barr Mansion in Austin, Texas. The two met in their early twenties and began their relationship around 2007, prior to Holiday's rise in the marketing and writing fields. They reside on a ranch outside Austin with their two sons, born circa 2016 and 2019. Holiday and his wife maintain a low public profile for their children, explicitly avoiding posting photographs or personal details online to shield them from digital exposure and potential algorithmic harms. This decision aligns with Holiday's broader writings on , where he emphasizes , , and modeling resilient behaviors over performative sharing. No public information is available regarding Holiday's parents or siblings.

Daily practices and influences

Holiday incorporates Stoic-inspired practices into his daily life, distinguishing between mere routines and intentional habits that foster resilience and focus. He wakes around 6 a.m. and begins with a three-mile walk, often with his children, followed by 15 minutes of journaling and reading a passage designed to impart wisdom, deliberately avoiding immediate engagement with email, , or to preserve mental clarity. Journaling, which he regards as the premier Stoic exercise, involves to process thoughts, clarify priorities, and confront potential challenges, echoing the introspective method of in his . Throughout the day, Holiday prioritizes deep work blocks for writing, interspersed with such as walking or exercise, lunch accompanied by reading, and administrative tasks deferred until later to maintain . Evenings emphasize family time and a wind-down routine to ensure restful sleep, underscoring his view that effective mornings depend on preparatory evenings free from overstimulation. He promotes additional habits like premeditating the day's actions upon rising—planning how to respond virtuously to events—and incorporating negative visualization to build , practices he adapts for modern application through his Daily platform. These routines stem primarily from the of ancient Stoics, including Epictetus's emphasis on controlling one's , Seneca's for deliberate , and Marcus Aurelius's to daily self-examination amid public duties. Holiday synthesizes these influences to advocate practices over inflexible schedules, arguing that repeatable actions like walking, reading primary sources, and ethical cultivate character regardless of varying circumstances. While he draws selectively from these historical figures—prioritizing their empirical observations over later interpretations—his approach integrates them with contemporary demands, such as family integration and creative output, without rigid adherence to ancient prescriptions.

Reception and Impact

Achievements and cultural influence

Holiday's writings have achieved substantial commercial success, with his Stoic-inspired titles collectively selling over six million copies and appearing on lists for more than 200 weeks. His book , published in 2014, resonated particularly in , influencing NFL coaches and players; Seattle Seahawks head coach and New England Patriots head coach reportedly drew from its principles during preparations for . The text has been credited with aiding Pittsburgh Steelers player Ryan Shazier's recovery mindset following a severe spinal injury in 2017. In addition to literary accomplishments, Holiday received a Grammy Award in 2017 for co-producing Ted Nash's Presidential Suite, which won in the Best Large Jazz Ensemble Album category. His marketing agency, Brass Check, has consulted for high-profile clients including Google and TASER, contributing to his reputation as a strategist bridging ancient philosophy with contemporary business practices. Recognized as one of Real Leaders' Top 50 Keynote Speakers in 2022, Holiday has delivered talks emphasizing Stoic virtues for leadership and decision-making. Holiday's cultural influence lies in popularizing as a practical framework for modern challenges, extending its reach beyond into , and corporate spheres. Through platform, which includes a with over 700,000 subscribers, he disseminates daily insights drawn from , , and , fostering a resurgence of the among executives, athletes, and public figures. Discussions with celebrities such as highlight 's application to personal resilience and craft mastery, amplifying its visibility in . This adaptation has drawn criticism for commercializing ancient texts but has undeniably broadened 's audience, positioning it as a tool for navigating ambition, adversity, and ethical conduct in high-stakes environments.

Criticisms and controversies

Holiday's 2012 book : Confessions of a Media Manipulator detailed his strategies for generating through fabricated stories and exploiting incentives, drawing significant backlash for endorsing deceptive practices. Reviewers on labeled him a "scumbag," while the described the revelations as "disturbing" and "chilling," arguing they undermined trust in . Holiday defended the work as an exposé on systemic flaws rather than a manual for harm, though critics contended it glorified manipulation during his tenure as marketing director for from 2009 to 2012. At , Holiday managed amid the company's scandals, including allegations against founder in 2011 and an immigration raid in 2008 that exposed undocumented workers, leading to 1,800 layoffs. The firm's provocative advertising campaigns, which Holiday later acknowledged as intentionally boundary-pushing, contributed to its reputation for toxicity, with Holiday navigating crises that exacerbated financial woes culminating in bankruptcy in 2015. reporting in 2012 highlighted Holiday's self-admitted role as a "media scammer," criticizing his tactics as emblematic of broader ethical lapses in . Holiday's popularization of Stoicism has faced philosophical critiques for oversimplifying ancient texts into motivational self-help, often prioritizing personal success over the tradition's emphasis on cosmic determinism and ego-dissolution. Commentators like Benjamin Cain argue that works such as The Obstacle Is the Way (2014) invert Stoic principles by framing adversity as a tool for ambition rather than acceptance, aligning more with existentialism or hustle culture. The Guardian noted recurring accusations that Holiday's commercial empire—encompassing books, courses, and merchandise—profits from diluting philosophy, though he counters that accessibility democratizes wisdom without compromising fidelity to sources like Marcus Aurelius and Seneca. In July 2021, Holiday sparked online debate by posting on about enforcing a no-mask policy at his bookstore, The Painted Porch, amid debates, with critics accusing him of politicizing health measures despite his advocacy for rationality. The article framed the episode as emblematic of broader cultural divides, though Holiday positioned it as a principled stand on local laws and personal autonomy. Additional detractors, including some Stoicism enthusiasts, have questioned his political commentary, such as criticisms of as a "failed businessman," as inconsistent with apolitical detachment.

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