Ep. 238 - Ryan Holiday: The Art of Making and Marketing

Ep. 238 - Ryan Holiday: The Art of Making and Marketing

Ryan Holiday, stop writing books that are just for me! With "Perennial Seller" you just answered an obsessive question I've had for years: What makes something, someone, some product, some art, withstand the test of time? What is the magic sauce? The secret formula? What makes something sell a million copies a year (music, art, books, products, etc)... forever? I want to know. I'll try my best to summarize our conversation and your book but people should buy the book for your 1000s of examples: BE COUNTERINTUITIVE If you write what everyone else is already thinking, then nobody needs to read your work, or use your product. They already have it. It doesn't matter if you are 50% better than anyone else. Nobody understands how to judge that except the experts in your field. And those experts don't care about you. They might even hate you. Create your own field. And be 1000% the best in that field. DON'T TRY TO COMPETE The 100th person who writes a "50 Shades of Grey" style book, or a disco pop EMD album can...MAYBE...get 1% of the audience. If you find an underserved audience, you can get 100% of it. There's an important side effect of this: IF YOU ARE DOING SOMETHING FOR THE MONEY...YOU LOSE. Because the rest of the world is competing for that dollar. Money is a side effect of creativity, quality art, creating something unique, and building your marketing into that art. VALIDATE THE IDEA Test out sample chapters. Release songs on YouTube. Keep iterating. Keep digging for your authentic voice. In comedy, it took Louis CK 20 years of telling jokes before he found his voice when talking about dating and parenting. Don't look for LOTs of fans at first. Look for the hard-core fans. The ones who will stick with you while you go on this crazy ride. The ones who will share. What my prior podcast guest, Kevin Kelly, calls "The One Thousand True Fans". DON'T GIVE UP IF YOU DON'T WIN ON DAY ONE Ryan told me that "Smokey and the Bandit" beat "Star Wars" at the box office the same weekend they both opened. I did not know that! It almost seems like blasphemy to me. John Grisham only sold a few thousand copies when he first published "A Time To Kill". Only much later did it sell millions. Catcher in the Rye had a slow start. Now sells a million copies a year. The best works of art and the best products have to fight the masses to find their right audience. But when they do, the audience will reward them. Write or create what is unique to you, find the 1000 true fans. The ones who are hard-core and love the value you bring. And serve that market over and over. That divides the winners from the non-winners. TELL A STORY THAT IS PERSONAL TO YOU "Choose Yourself" could have been another ranty personal development business book ("Blah!"). Instead I wove in a personal story of struggle and loss and pain. Pain that changed me and still does every single day to (hopefully) lesser extent. This is what makes a story both unique (it's my story) and universal (everyone experiences pain, everyone wants to solve it). Too many people play a persona ("my life is perfect so let me teach it to you") and that's inauthentic. TELL A STORY THAT RESONATES WITH EVERYONE Star Wars is a perfect example. It's the 'arc of the hero'. A boy who struggles, encounters problems, faces them, lives forever. I.e. Jesus. Krishna. Buddha. Star Wars is a sci-fi western (great example of "idea sex") where he innovated on the graphics but used a story that was basically "Focus grouped" for thousands of years. Thousands! So he stuck within the rules of a genre (actually several that he combined) but also made it uniquely his own. This is the key to successful art. Telling a story that is personal to you AND resonates with everyone is very difficult. It takes practice. It takes marketing. It takes listening. That's why these are the items that become perennial sellers. It's worth... See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Is Mind-Reading AI Coming Soon? My First Real AI Nervous Moment

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“If You’re Still Trying to Be Rational Now, You’re Crazy:” Comedian Tim Dillon on Being Informed vs. Being Ignorant

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A Note from James:Tim Dillon is crazy—in the best way. Not “institution” crazy. Crazy smart. Years ago he told me things about Epstein, hustle culture, and how the world really works that felt outland...

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How to Challenge Moon Landing Hoax Theories: Insights from Brian Keating

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James brings back astrophysicist Brian Keating for a practical takedown of moon-landing conspiracy claims—and a wider lesson in how to reason when everyone has a microphone. From the Van Allen belts t...

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