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Leadership keynote speakers

Ryan Holiday

Number One New York Times Bestselling Author, Founder of Daily Stoic, and Modern Stoicism's Leading Voice

Speaking feeTypically $50k–$100kIndicative only, confirmed on request
  • Keynote · Fireside chat · Moderation
  • English
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Headliner can arrange a booking with Ryan Holiday or their representative. This profile is compiled from public sources; availability and fees are confirmed on request. A listing here does not imply endorsement, affiliation, partnership, or exclusivity.

Signature keynotes

What your audience walks away with

  • Outcome

    Stoicism, What Ancient Wisdom Can Teach Us

    The foundational talk. Ryan draws on 2,300 years of Stoic philosophy, practiced by emperors, generals, and writers facing real stakes, and translates it into a practical toolkit for clarity, resilience, and peace of mind under modern pressure. The talk that introduces every other idea in his catalog.

  • The Four Virtues of Stoic Leadership

    Wisdom, courage, discipline, and justice: the four cardinal Stoic virtues, drawn from his completed four-book Stoic Virtues series, applied directly to how leaders make decisions, build character, and run teams that hold up under pressure.

  • Ego Is the Enemy: Leading Without Losing Yourself

    How unchecked ego derails high performers and organizations at every stage, aspiring, arriving, and failing, and the discipline it takes to keep learning and growing instead of coasting on past success.

  • The Obstacle Is the Way

    His most widely known idea: how to turn setbacks into strategic advantage. Built on historical and contemporary case studies, this is the talk that introduced millions of readers, and entire sports organizations and military units, to practical Stoicism.

  • Wisdom Takes Work: Building Judgment in an Age of Distraction

    Drawn from the closing volume of his Stoic Virtues series: wisdom as the master virtue, built through a lifelong cycle of learning, listening more than talking, and ruthlessly questioning your own certainty. A sharp fit for leaders navigating noisy, high-distraction environments.

  • Lasting Impact

    What separates work, and brands, that endure from what simply trends and fades. Drawn from his marketing background and his book Perennial Seller, this talk applies Stoic patience to building something that lasts.

The story

Who Ryan actually is

Ryan Holiday dropped out of the University of California, Riverside at nineteen and moved to Los Angeles, where he began working as a research assistant to Robert Greene, author of The 48 Laws of Power. From there he became Director of Marketing at American Apparel, a role that put him at the center of some of the most talked-about (and most studied) marketing campaigns of the era, before he left in 2014 to start his own firm. That same year, he published The Obstacle Is the Way, the book that introduced practical Stoic philosophy to a new generation of readers, from Silicon Valley entrepreneurs to professional sports locker rooms. Ego Is the Enemy followed in 2016, and The Daily Stoic, a book of daily meditations, became the foundation for what is now Daily Stoic: a media platform reaching hundreds of thousands of people through a daily email, a podcast, and a growing library of video content. Over the past decade, Ryan built out what is now a complete body of work: a four-book "Stoic Virtues" series, one book for each cardinal Stoic virtue, starting with Courage Is Calling (2021), Discipline Is Destiny (2022), and Right Thing, Right Now (2024, an instant #1 New York Times bestseller), and closing with Wisdom Takes Work in 2025. Across sixteen books, his work has sold more than ten million copies in over 40 languages. In 2021, Ryan and his wife opened The Painted Porch Bookshop in Bastrop, Texas, a small-town independent bookstore he built and still personally curates on his own ranch outside Austin. It's become as much a part of his public identity as his books: proof, in his words, that the same patient, disciplined principles he writes about apply to building something real and lasting, not just writing about it. Today, Ryan speaks to a genuinely wide range of audiences, from corporate leadership teams at companies like Google and Nike, to professional and collegiate sports organizations, to military audiences, bringing the same core message wherever he goes: that the obstacles you face aren't the exception to a good life or a good career, they're the material of it.

The receipts

Books & publications

  • The Obstacle Is the Way

    2014

    (2014): The book that introduced modern Stoicism to a mainstream business and sports audience; the idea that what stands in the way becomes the way.

  • Ego Is the Enemy

    2016

    (2016): How unchecked ego undermines learning, growth, and long-term success, at every stage of a career.

  • Stillness Is the Key

    2019

    (2019): Why mental stillness, not constant motion, is the real competitive advantage for high performers.

  • Right Thing, Right Now

    2024

    (2024): The third book in the Stoic Virtues series, on justice; an instant #1 New York Times bestseller.

  • Wisdom Takes Work

    2025

    (2025): The closing volume of the Stoic Virtues series, on how real judgment is built through a lifelong cycle of learning, applying, and repeating.

  • Trust Me, I'm Lying

    2012

    (2012): His debut, a candid account of modern media manipulation drawn from his own marketing career.

Gravity

Career highlights & recognition

  • Recognition

    #1 New York Times bestselling author

    of sixteen books, over ten million copies sold in 40+ languages

  • Credential

    Founder of Daily Stoic

    a media platform reaching 200,000+ daily newsletter subscribers and a podcast averaging roughly 3 million downloads a month

  • Milestone2021

    Completed the four-book "Stoic Virtues" series

    Courage Is Calling, Discipline Is Destiny, Right Thing, Right Now, and Wisdom Takes Work (2021 to 2025)

  • Recognition

    Named to Real Leaders' Top 50 Keynote Speakers in the World

  • Credential

    Former Director of Marketing, American Apparel

    author of Trust Me, I'm Lying, his account of modern media manipulation

  • Credential2021

    Owner and operator, The Painted Porch Bookshop

    Bastrop, Texas (opened 2021)

  • Milestone

    Google, Nike, and Goldman Sachs

    professional and collegiate sports organizations, and U.S. military and government audiences

  • Milestone2025

    sold-out international speaking tour in 2025

    following the release of Wisdom Takes Work, with the "Daily Stoic Live" tour continuing into 2026

Booking with confidence

What to expect when you book Ryan

  • 01

    Compiled from public sources

    This profile is built from public, verifiable material and stamped with the date it was last reviewed. Nothing here is a claim we cannot trace to a source.

  • 02

    Availability and fees, confirmed

    Tell us your date and brief, and we confirm Ryan's availability and current fee on request. We never publish a fabricated figure or imply an exclusivity we do not hold.

  • 03

    Managed end to end

    From first inquiry to the day itself, Headliner handles briefing, contracting, and logistics, so your team can focus on the event.

Answers

Booking questions, answered

What is Ryan Holiday's speaking fee?

Typically $50k–$100k (indicative; confirmed on request). Ryan's fee varies by event, date, format, and location, so we confirm the exact figure for your booking. Share your brief for current pricing and live availability.

Is Ryan Holiday available for my event date?

Availability changes with Ryan's schedule and the season. Tell us your date and we'll confirm whether Ryan is open, and hold the slot while you decide.

How do I book Ryan Holiday for my event?

Ryan Holiday is booked through Headliner. Tell us your event date, audience, and goals, and we'll confirm availability and the next steps, typically within four business hours.

How much does Ryan Holiday charge to speak?

Typically $50k–$100k (indicative; confirmed on request). It depends on event, date, format, location, and whether the session is in person or virtual. Share your brief and we'll confirm the exact figure and availability.

Can I hire Ryan Holiday for a corporate event?

Yes. Ryan is represented for speaking engagements through Headliner on a non-exclusive basis and regularly takes corporate keynotes, conferences, and leadership events. Share your brief to check availability.

Can I book Ryan Holiday for a virtual keynote?

Yes. Ryan presents virtual keynotes as well as in-person sessions. Virtual fees are typically quoted below a live keynote, so tell us your format for a precise quote.

What formats does Ryan offer?

Ryan is available for Keynote, Fireside chat, Moderation and Virtual engagements. We'll match the format to your audience and run-of-show.

What does Ryan speak about?

Ryan's keynote themes include Team & Culture, Transformation and Mindset. Each talk is tailored to your audience and outcomes.

What languages does Ryan present in?

Ryan presents in English.

Where does Ryan travel from?

Ryan is based in Austin, TX and travels internationally for engagements; virtual sessions are also available.

Profile updated . Compiled from public sources; confirm current fees and availability with Headliner.

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