Robert Greene & Ryan Holiday: The Secret To A Great Apprenticeship
- 20m
- Transcript
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
- 0:00Podcast 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.
- 1:07Ryan 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.
- 2:12Why 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.
- 3:17Entry‑Level Work and AI Disruption
The conversation turns to how AI is eliminating entry‑level roles that traditionally serve as apprenticeship gateways.
- 5:00Writing, 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.
- 9:00Closing Thoughts and Final Takeaways
Ryan wraps up with final reflections on the apprenticeship model and encourages listeners to seek or create meaningful learning relationships.
- 11:53Personal 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.
- 17:38The 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.
- 22:46Creating Your Own Mentorship When None Exists
Greene explains how to emulate a mentor by studying historical figures and internalizing their strategies.
Highlights
- 1:06
The Power of an Apprenticeshipstory
The host reflects on how meeting the guest as a college dropout changed his life and launched his writing career.
- 2:15
Trusting Non-Verbal Cuesinsight
The guest explains that he hired the host because he sensed genuine seriousness amidst many applicants chasing fame.
- 3:17
AI Replacing Entry-Level Workinsight
The discussion highlights how automated transcription and AI eliminate standard entry-level tasks, raising the stakes for human assistants.
- 8:10
The Core Duty of an Apprenticestrategy
The guest emphasizes that an apprentice must find out what skills the mentor lacks and supply them to create dependency.
- 8:58
The Indispensable Value of Writinginsight
The guest argues that learning how to write is essential across nearly all fields because it reflects the ability to think.
- 13:01
Learning the Etiquette of Silencestory
The host shares a story about a boss who taught him that speaking up in meetings should be reserved for necessity rather than ego.
- 19:40
Wearing the Wrong Uniformstory
The host recounts an early job interview where he wore a suit to a record label and completely misread the cultural uniform.
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
Sponsored segments
- 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
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