Summer School: Ryan Holiday on Stoicism, Marketing, and Creating Work That Lasts

Hey friends, Chase here.
Every summer, I revisit conversations from the archive that have stood the test of time. Not because I'm nostalgic, but because the best ideas don't expire. They deepen. This is another installment of Summer School—the set of episodes I personally return to the most when I'm stuck and need something true to lean on. This one with Ryan Holiday is high on that list. I've gone back to it multiple times this year alone. Ryan is a legend—author, media strategist, New York Times bestselling writer, and the person who brought Stoic philosophy into popular culture for a generation of creatives and entrepreneurs. This conversation is from 2017, before he'd fully hit the stride we know him for now. He'd already published something like six books in five years. He was already a force. And yet you can hear, in this episode, exactly where his work was headed. What stands out isn't just marketing tactics. It's framing. Good marketing isn't only writing good copy or taking a nice product photo. It's making work that starts a discussion. It's asking better questions before you begin. And it's using your own mindset—perception, action, will—to keep going when the creative path gets hard. Those tools were spot on then. They're truer now.
Nobody cares what you're thinking about doing. Talk about your ideas after you've started them and then show people what you've done.
Summer School: Ryan Holiday on Stoicism, Marketing, and Creating Work That Lasts
Ryan dropped out of college at 19 to work with Robert Greene, became director of marketing at American Apparel, and later built Brass Check, advising clients like Google, Tim Ferriss, and Tony Robbins. Then he did something that looked, on paper, like career suicide: he wrote Trust Me, I'm Lying—a book about how marketers, companies, and politicians manufacture and manipulate attention online. Instead of burning his marketing career down, it opened writing as a profession. He began identifying as a writer first—keeping a hand in marketing so he wouldn't only comment from the sidelines. That tension runs through the whole episode: how information spreads, what it means to compete for attention, and how to build work that doesn't disappear after the launch week. At the center is Perennial Seller—the art of making and marketing work that lasts. Not the fidget-spinner hit. Not the trend piece. The Original Pantry Cafe that never closes. The book that sells more copies year after year because it solves a real problem. The boot that gets better the longer you wear it. If you're a creator, entrepreneur, or leader trying to make something that matters—and survive the noise long enough for it to land—this episode is still one of the sharpest in the archive.
What You'll Hear in This Episode
Why Ryan left New York for a cattle ranch outside Austin—and how distance, physical work, and humility made him better at the cerebral work
How Trust Me, I'm Lying mapped the attention economy years before "fake news" became a daily phrase
Why modern marketing is less about perfect product shots and more about starting conversations
A practical crash course in Stoicism: perception, action, and will
Ego vs. confidence—and how to market without marketing to yourself
Austin Kleon's line: you can't be the noun without doing the verb
What makes a perennial seller—and why industries obsess over "new" while most of their money comes from what lasts
The "other 50%": craft gets you in the door; packaging, positioning, relationships, and community finish the race
Two questions before every project: Who is this for? What does this do for them?
Three Stoic Disciplines for Creatives
Ryan's version of Stoicism is deliberately practical. Not academic debate—the art of living. Philosophy for the role you're already in: photographer, founder, writer, leader. He walks through three disciplines:
1. Perception
How do you look at the situation? Someone is rude. Your company is in trouble. Your work isn't getting seen...