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

Oct 24, 2026 21 min

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 <a href="https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=4&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">The 48 Laws of Power</a>, <a href="https://www.thepaintedporch.com/products/mastery-signed-by-robert-greene?_pos=3&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">Mastery</a>, <a href="https://www.thepaintedporch.com/products/laws-of-human-nature-copy?_pos=2&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">The Laws of Human Nature</a>, and his new book <a href="https://www.thepaintedporch.com/products/the-law-of-the-sublime?_pos=13&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">The Law of the Sublime </a>, 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 <a href="https://www.thepaintedporch.com/products/the-law-of-the-sublime?_pos=13&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">The Law of the Sublime by Robert Greene</a> | <a href="https://www.thepaintedporch.com/products/the-law-of-the-sublime?_pos=13&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">https://www.thepaintedporch.com/products/the-law-of-the-sublime?_pos=13&_sid=e0d7a8c03&_ss=r</a> Grab signed copies of Robert Greene’s books at The Painted Porch: <a href="https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=4&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">The 48 Laws of Power</a> | <a href="https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=4&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=4&_sid=e0d7a8c03&_ss=r</a> <a href="https://www.thepaintedporch.com/products/laws-of-human-nature-copy?_pos=2&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">The Laws of Human Nature</a> | <a href="https://www.thepaintedporch.com/products/laws-of-human-nature-copy?_pos=2&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">https://www.thepaintedporch.com/products/laws-of-human-nature-copy?_pos=2&_sid=e0d7a8c03&_ss=r</a> <a href="https://www.thepaintedporch.com/products/mastery-signed-by-robert-greene?_pos=3&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">Mastery</a> | <a href="https://www.thepaintedporch.com/products/mastery-signed-by-robert-greene?_pos=3&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">https://www.thepaintedporch.com/products/mastery-signed-by-robert-greene?_pos=3&_sid=e0d7a8c03&_ss=r</a> <a href="https://www.thepaintedporch.com/products/33-strategies-of-war-signed-by-robert-greene?_pos=5&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">The 33 Strategies of War</a> | <a href="https://www.thepaintedporch.com/products/33-strategies-of-war-signed-by-robert-greene?_pos=5&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">https://www.thepaintedporch.com/products/33-strategies-of-war-signed-by-robert-greene?_pos=5&_sid=e0d7a8c03&_ss=r</a> <a href="https://www.thepaintedporch.com/products/art-of-seduction-signed-by-robert-greene?_pos=6&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">The Art of Seduction</a> | <a href="https://www.thepaintedporch.com/products/art-of-seduction-signed-by-robert-greene?_pos=6&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">https://www.thepaintedporch.com/products/art-of-seduction-signed-by-robert-greene?_pos=6&_sid=e0d7a8c03&_ss=r</a> <a href="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" rel="noopener noreferrer" target="_blank">The Daily Laws: 366 Meditations on Power, Seduction, Mastery, Strategy, and Human Nature</a> | <a href="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" rel="noopener noreferrer" target="_blank">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</a> <a href="https://www.thepaintedporch.com/products/50th-law-signed-by-robert-greene?_pos=10&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">The 50th Law</a> | <a href="https://www.thepaintedporch.com/products/50th-law-signed-by-robert-greene?_pos=10&_sid=e0d7a8c03&_ss=r" rel="noopener noreferrer" target="_blank">https://www.thepaintedporch.com/products/50th-law-signed-by-robert-greene?_pos=10&_sid=e0d7a8c03&_ss=r</a> Follow Robert Greene <a href="https://www.instagram.com/robertgreeneofficial/?hl=en" rel="noopener noreferrer" target="_blank">Instagram</a> | <a href="https://www.instagram.com/robertgreeneofficial/?hl=en" rel="noopener noreferrer" target="_blank">https://www.instagram.com/robertgreeneofficial/?hl=en</a> <a href="https://x.com/RobertGreene" rel="noopener noreferrer" target="_blank">X</a> | <a href="https://x.com/RobertGreene" rel="noopener noreferrer" target="_blank">https://x.com/RobertGreene</a> <a href="https://www.youtube.com/@RobertGreeneOfficial" rel="noopener noreferrer" target="_blank">YouTube</a> | <a href="https://www.youtube.com/@RobertGreeneOfficial" rel="noopener noreferrer" target="_blank">https://www.youtube.com/@RobertGreeneOfficial</a> 🎟️<a href="https://www.dailystoiclive.com/" rel="noopener noreferrer" target="_blank"> </a><a href="https://www.dailystoiclive.com/" rel="noopener noreferrer" target="_blank">DAILY STOIC LIVE </a>| Ryan Holiday is coming to a <a href="https://www.dailystoiclive.com/" rel="noopener noreferrer" target="_blank">city near you</a>! 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