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...
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. Do you decide it's unfair, impossible, purely negative—or do you look for what you can actually use?
The Stoics' move: there's no inherent good or bad—there's how we look at things. We don't control most of what happens to us. We do control the last crucial part: what we tell ourselves it means.
Marcus Aurelius did that work through writing—Meditations as a private practice of catching your own mind in the act.
2. Action
Seeing differently isn't enough. What do you do with the information?
Ryan's favorite cut: Casey Neistat telling someone pitching a business idea, essentially—don't tell me the idea. Tell me when you've started it, then show me what you've made. Thinking about running a marathon doesn't count. Starting does.
This is the discipline that kills the fantasy. Ideas are cheap. Execution is the only proof.
3. Will
How do you handle the moments when life kicks your ass and you can't reverse them?
Ryan tells the Edison story: factory on fire, son shell-shocked, Edison telling him to get his mother—she'll never see a fire like this again. Even what you can't control can still transform you. Hardship is often the filter that keeps everyone who doesn't want it as badly as you do from finishing.
If it were easy, there'd be more amateurs—and less value.
Perennial Seller (and the Other 50%) The face-palm insight behind Perennial Seller: the New York Times bestseller list doesn't track perennial sellers—yet a huge share of publishing income comes from books that came out years or decades ago. Industry attention chases "new." Durable value often lives elsewhere.
Ryan's frame for durable work is almost annoyingly clear: This is a blank that does blank for blank.
Who is it for—really? Not "everyone" or "smart people." Actual humans. Where they live. What they do.
What does it do for them? His editor's line: it's not what a book is—it's what a book does.
Then comes Chase's "other 50%," which Ryan amplifies: making the thing is a marathon. Finishing it doesn't mean you've won. There's a second marathon waiting—marketing, packaging, relationships, platform, the bridge from your desk into someone else's life. "If you build it, they will come" has killed a lot of great work. You're not just competing with peers who launched this week. You're competing with time-tested work that already lives on Netflix, in bookstores, in cultural memory.
Title, cover, logo, copy, collaborators—these aren't afterthoughts. They're part of the creative expression. Books have covers because people judge them. Your work does too.
And if you're already hunting for shortcuts before you've started? That's a signal. Principles over formulas. The shortcuts get exploited the moment they work for everyone.
Timecodes So You Can Jump Around - 00:00 – Welcome and why this episode is part of Summer School
- 04:52 – Ryan Holiday joins; life on a ranch outside Austin
- 09:14 – From renegade marketer to writer: Trust Me, I'm Lying and how attention spreads
- 15:05 – Why marketing today means starting a discussion
- 16:58 – Stoicism as a practical art of living
- 21:54 – Discipline one: perception
- 25:34 – Discipline two: action (start it, then show it)
- 28:47 – Discipline three: will (Edison's fire and transforming hardship)
- 31:36 – Ego vs. confidence; marketing without marketing to yourself
- 37:01 – Fall in love with the verb, not the noun
- 40:14 – Perennial Seller: the art of making work that lasts
- 47:08 – "This is a blank that does blank for blank"
- 51:07 – Habits of people who make great work (editors, collaborators, objectivity)
- 54:47 – The other 50%: craft plus packaging, relationships, and community
- 01:04:35 – Frameworks: Who is this for? What does this do?
- 01:19:05 – Daily Stoic, memento mori, and closing thoughts
Why This Conversation Still Matters In 2017, Ryan was already describing an attention landscape where your best work competes with cats, outrage, porn, fake news, and infinite other options in the feed. That landscape didn't calm down. It accelerated.
What still cuts through is the opposite of trend-chasing: work built on timeless problems, principles that survive platform changes, and the humility to keep doing the verb while everyone else celebrates the noun.
When I'm stuck—when the world feels noisy and my own next project feels either too precious or too thin—I come back to this episode for the same reminders:
Control how you see it. Take action. Let the hard parts transform you. Ask who it's for and what it does. Don't confuse finishing the making with finishing the work. Fall in love with the craft more than the identity. And don't wait until you feel safe to do the honest version of the thing.
That's why it's Summer School material. The platforms changed. The books multiplied. The stakes got louder. The questions held.
Keep Going Deeper If this conversation resonates:
- Perennial Seller: The Art of Making and Marketing Work That Lasts
- The Obstacle Is the Way
- Ego Is the Enemy
- Trust Me, I'm Lying
- Daily Stoic: dailystoic.com
- Ryan online: ryanholiday.net
Follow Ryan: Website | X/Twitter | Facebook
Questions to Reflect On - Am I still stuck in "thinking about" the project—or have I started something I can show?
- Where am I treating a hard situation as a verdict, instead of as information I can act on?
- Am I marketing to an audience—or marketing to myself?
- Have I fallen in love with the noun (author, founder, photographer) more than the verb?
- If I had to fill in "This is a ___ that does ___ for ___," could I do it clearly—today?
- Where have I finished the making and abandoned the second marathon: positioning, packaging, relationships, community?
- Am I building on timeless problems—or on platforms and tactics that may not survive the next cycle?
The Core Idea Work that lasts isn't the work that wins the news cycle. It's the work that keeps solving something real for someone specific—long after the launch adrenaline fades.
Ryan's invitation in this conversation is both simple and demanding: sharpen your perception, take action before you announce, let difficulty refine you, kill the ego that wants applause without evidence, and build for durability instead of novelty.
If there's one lesson worth carrying forward from this Summer School session, it's this:
Make something that starts a conversation—and lasts long enough to deserve one.
