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Robert Greene & Ryan Holiday: The Secret To A Great Apprenticeship

The Daily Stoic | Wondery+

20m
Transcript

Original podcast

Summary

Written by a model from the transcript; not yet reviewed.

This episode explores the mechanics of a great apprenticeship and career mentorship, featuring a retrospective discussion between host Ryan Holiday and author Robert Greene on their working relationship that began twenty years ago. The conversation examines the changing landscape of entry-level positions in the era of artificial intelligence, arguing that while tools like automated transcription eliminate traditional footing, the fundamental human qualities of an apprentice remain rare and vital. The speakers analyze why apprenticeships succeed or fail, breaking down the importance of ego reduction, self-awareness, and understanding the self-interest of mentors. Through specific anecdotes from early career missteps, the discussion outlines actionable rules for young professionals looking to earn trust, avoid common traps, and genuinely help busy mentors save time.

  • Prioritize saving time and reducing stress for the person you work for rather than seeking attention for yourself. 5:24
  • Develop strong writing skills because writing requires critical thinking that automated tools cannot replicate with soul. 8:58
  • Cultivate social skills to successfully navigate multi-generational workplaces and understand how older colleagues perceive you. 7:19
  • Appeal directly to a mentor's self-interest instead of relying on emotional sob stories or appeals for mercy. 17:49

Chapters

  1. 0:00
    Podcast Intro and Airbnb Travel Tips

    Ryan Holiday opens the episode with a personal travel update and shares how Airbnb stays helped him write and learn new things.

  2. 1:07
    Ryan Meets Robert Greene and Apprenticeship Beginnings

    Ryan recounts how a college dropout was hired by Robert Greene as a research assistant, setting the stage for a life-changing apprenticeship.

  3. 2:12
    Why Robert Greene Hired Ryan

    Ryan asks Greene why he chose him, and Greene explains his intuition and the importance of a short leash in early hires.

  4. 3:17
    Entry‑Level Work and AI Disruption

    The conversation turns to how AI is eliminating entry‑level roles that traditionally serve as apprenticeship gateways.

  5. 5:00
    Writing, Thinking, and Social Skills as Core Apprenticeship Skills

    Ryan and Greene discuss why writing, critical thinking, and interpersonal skills are essential for apprentices in a world dominated by AI.

  6. 9:00
    Closing Thoughts and Final Takeaways

    Ryan wraps up with final reflections on the apprenticeship model and encourages listeners to seek or create meaningful learning relationships.

  7. 11:53
    Personal Anecdotes: Mistakes and Lessons Learned

    Ryan shares real‑world blunders—offending a partner and misreading social cues—and how they taught him the value of humility and observation.

  8. 17:38
    The 48 Laws of Power and Apprenticeship Dynamics

    The hosts examine how Greene’s own book influenced Ryan’s career and the importance of appearing helpful rather than self‑interested.

  9. 22:46
    Creating Your Own Mentorship When None Exists

    Greene explains how to emulate a mentor by studying historical figures and internalizing their strategies.

Highlights

Quotes

  • “That's the power of an apprenticeship. That's the power of a great mentor.”
    Unnamed speaker · 1:36
  • “You have to be emotionally engaged. But your job is not about your ego. It's not about getting attention.”
    Robert Greene · 5:20
  • “If you save them time, they're gonna become dependent on you.”
    Robert Greene · 6:01
  • “Learn how to write. It'll be a skill that, I don't care what field you're in, unless you're going into plumbing, that being able to write won't be a critical skill.”
    Robert Greene · 9:05
  • “You have to be aware that people are looking at you and judging you.”
    Robert Greene · 19:04
  • Airbnb 0:09–1:11
  • Wayfair 16:03–17:09
  • Superhuman Go 23:26–23:52

About this episode

Twenty years ago, Robert Greene took a chance on a young college dropout named Ryan Holiday. In this episode, Ryan sits down with Robert, bestselling author of The 48 Laws of Power https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=4&_sid=e0d7a8c03&_ss=r, Mastery https://www.thepaintedporch.com/products/mastery-signed-by-robert-greene?_pos=3&_sid=e0d7a8c03&_ss=r, The Laws of Human Nature https://www.thepaintedporch.com/products/laws-of-human-nature-copy?_pos=2&_sid=e0d7a8c03&_ss=r, and his new book The Law of the Sublime https://www.thepaintedporch.com/products/the-law-of-the-sublime?_pos=13&_sid=e0d7a8c03&_ss=r, to reflect on the power of apprenticeship, the lessons that shaped his career, the mistakes that nearly derailed it, and what it takes to learn from someone great. Preorder The Law of the Sublime by Robert Greene https://www.thepaintedporch.com/products/the-law-of-the-sublime?_pos=13&_sid=e0d7a8c03&_ss=r | https://www.thepaintedporch.com/products/the-law-of-the-sublime?_pos=13&_sid=e0d7a8c03&_ss=r https://www.thepaintedporch.com/products/the-law-of-the-sublime?_pos=13&_sid=e0d7a8c03&_ss=r Grab signed copies of Robert Greene’s books at The Painted Porch: The 48 Laws of Power https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=4&_sid=e0d7a8c03&_ss=r | https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=4&_sid=e0d7a8c03&_ss=r https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=4&_sid=e0d7a8c03&_ss=r The Laws of Human Nature https://www.thepaintedporch.com/products/laws-of-human-nature-copy?_pos=2&_sid=e0d7a8c03&_ss=r | https://www.thepaintedporch.com/products/laws-of-human-nature-copy?_pos=2&_sid=e0d7a8c03&_ss=r https://www.thepaintedporch.com/products/laws-of-human-nature-copy?_pos=2&_sid=e0d7a8c03&_ss=r Mastery https://www.thepaintedporch.com/products/mastery-signed-by-robert-greene?_pos=3&_sid=e0d7a8c03&_ss=r | https://www.thepaintedporch.com/products/mastery-signed-by-robert-greene?_pos=3&_sid=e0d7a8c03&_ss=r https://www.thepaintedporch.com/products/mastery-signed-by-robert-greene?_pos=3&_sid=e0d7a8c03&_ss=r The 33 Strategies of War https://www.thepaintedporch.com/products/33-strategies-of-war-signed-by-robert-greene?_pos=5&_sid=e0d7a8c03&_ss=r | https://www.thepaintedporch.com/products/33-strategies-of-war-signed-by-robert-greene?_pos=5&_sid=e0d7a8c03&_ss=r https://www.thepaintedporch.com/products/33-strategies-of-war-signed-by-robert-greene?_pos=5&_sid=e0d7a8c03&_ss=r The Art of Seduction https://www.thepaintedporch.com/products/art-of-seduction-signed-by-robert-greene?_pos=6&_sid=e0d7a8c03&_ss=r | https://www.thepaintedporch.com/products/art-of-seduction-signed-by-robert-greene?_pos=6&_sid=e0d7a8c03&_ss=r https://www.thepaintedporch.com/products/art-of-seduction-signed-by-robert-greene?_pos=6&_sid=e0d7a8c03&_ss=r The Daily Laws: 366 Meditations on Power, Seduction, Mastery, Strategy, and Human Nature https://www.thepaintedporch.com/products/the-daily-laws-366-meditations-on-power-seduction-mastery-strategy-and-human-nature-copy?_pos=7&_sid=e0d7a8c03&_ss=r | https://www.thepaintedporch.com/products/the-daily-laws-366-meditations-on-power-seduction-mastery-strategy-and-human-nature-copy?_pos=7&_sid=e0d7a8c03&_ss=r https://www.thepaintedporch.com/products/the-daily-laws-366-meditations-on-power-seduction-mastery-strategy-and-human-nature-copy?_pos=7&_sid=e0d7a8c03&_ss=r The 50th Law https://www.thepaintedporch.com/products/50th-law-signed-by-robert-greene?_pos=10&_sid=e0d7a8c03&_ss=r | https://www.thepaintedporch.com/products/50th-law-signed-by-robert-greene?_pos=10&_sid=e0d7a8c03&_ss=r https://www.thepaintedporch.com/products/50th-law-signed-by-robert-greene?_pos=10&_sid=e0d7a8c03&_ss=r Follow Robert Greene Instagram https://www.instagram.com/robertgreeneofficial/?hl=en | https://www.instagram.com/robertgreeneofficial/?hl=en X https://x.com/RobertGreene | https://x.com/RobertGreene YouTube https://www.youtube.com/@RobertGreeneOfficial | https://www.youtube.com/@RobertGreeneOfficial 🎟️https://www.dailystoiclive.com/DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://dailystoic.com/dailyemail -- Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

Transcript

0:00
20:31

4,630 words · 6 speakers

Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.

Topics

  • AI
  • American Apparel
  • 48 Laws of Power
  • Hollywood
  • Verizon FiOS
  • San Diego
  • The Law of the Sublime
  • The Wisdom Book

Page updated · transcript and summary are machine-generated