You know him as the CEO of OpenAI — but did you know that Sam Altman is an avid writer?  As one of today’s most successful entrepreneurs, Sam champions the tremendous value of writing: how it clarifies your thinking, expands your ideas, and levels-up your life in every sense, both personally and professionally. Plus, he has a love for the creative. (Have you ever met someone who can recite Percy Bysshe Shelley poems from memory? Well, Sam can.)  In this episode, we discuss how Sam uses...

Robert went from being “a drunk, failed screenwriter” to writing seven bestsellers with millions of copies sold. Entrepreneurs, politicians, and hip-hop artists like 50 Cent all love his work. His secret ingredient? Storytelling. In Robert’s eyes, story is a form of seduction. So, welcome to 76-minutes of seductive storytelling advice. You’ll learn how to write stories that have timeless resonance, swapping cute and clever for crisp and clear. You’ll dive deep into style, themes, research,...

Welcome to 74-minutes of storytelling strategy that’s better than all of your English classes combined. Nick is a journalist who has written for The New York Times and Vanity Fair. He’s a screenwriter, an author, a murder mystery enthusiast. In other words, he knows how to push a story through a brick wall. And he’s going to show you how you can, too.  This episode is the ultimate storytelling toolkit. Cliffhangers. Tension. Dialogue. Character. Motifs. You’ll learn it all.  And here’s the...

“I’ll never forget the first patient whom I ever saw die.” Sheesh, what an opening line, right? Peter has an outstanding resume: he’s a medical surgeon, a Stanford grad, and a longevity expert with 25+ years of industry experience — not to mention, a published author who has sold over two million copies of his book, Outlive.  In a nutshell, Peter is a prime example of what can happen when you share your expertise through writing. And he’s going to help you get started.  In this episode,...

What if writing a newsletter could pay your rent? Well, it can. And today, you’re going to learn how. Ben Thompson makes millions of dollars a year with his writing. He’s the OG of subscription-based newsletter writers. Maybe that’s your dream, too, but you’re plagued by questions like: “What should I write about?” “What’s my business model?” “How do I make my first dollar online?” We’re so glad you asked; because Ben has the answers. In this episode, you’ll learn his exact playbook for how...

Ever thought to yourself, “I would love to write a memoir someday”?  Then you’re in the right place. Rob has an exceptional story — from foster care to Yale, from a troubled childhood to a best-selling memoir called Troubled — and in this episode, he demystifies the memoir-writing process just for you.   We cover questions like: Which stories are worthy of sharing? How do you pace the narrative? How do you excavate difficult memories? How do you balance the emotional highs with the lows?...

Your success as a writer boils down to your style. And today, you’re going to learn how to master the two different types of style — minimalism vs. maximalism — from the style-king himself: The Cultural Tutor.  Minimalism is clear, concise, and direct. It distills an idea. Maximalism captures the texture, the nuance, the beauty of life. It creates an environment for your reader to inhabit. Style is a spectrum. And the sweet spot of memorable writing comes from the tension of competing forces...

What do Katy Perry, Charles Dickens, and the Bible all have in common? They’re responsible for some of the most famous lines in history. And in this episode, you’ll find out why.  Mark, an author and mad scientist of language, reveals the secret sauce to memorable writing: rhetorical devices. Chiasmus. Anaphora. Antithesis. Synecdoche.  Writing today (i.e. texting and Tweeting) is concise and hyper-minimal — which is fine, if you’re writing the instruction manual for a new dishwasher. But...

Harry is a master copywriter — and that’s not hyperbole. With Marketing Examples, he’s taught over 100,000 people how to write copy that rips. And guess what? You’re next.  Copywriting is the wrapper of success for every company. It’s the difference between Snickers, the bestselling chocolate bar in the world (“You’re not you when you’re hungry”) and a chocolate bar that looked and tasted just like Snickers, but went out of business in 2006. (Ever had a Fuse bar? Yeah, neither have we.)  Good...

Scott is a cocktail of crass humor, brutal honesty, and millionaire advice. He spent ten years wanting to write a book, and when he finally did, everything he learned could be summed up into two words: Be fearless.  So buckle up — because today, you’re going to learn how to write fearlessly.  In this episode, we break down the nitty-gritty mechanics of fearless writing: how to create intimacy with your reader, how to craft a narrative, how to share bold opinions, how to use humor as a weapon,...

Two words: Storytelling. Masterclass.  Yeah, yeah, we know — “become a better storyteller” is probably the most basic writing advice out there. But this episode is far from basic. It’s all about the storytelling advice you actually need that you didn’t get in school. Once upon a time, Nat wrote online SEO blogs: simple, generic, and kind of boring. What he really wanted was to write a memoir: something narrative, beautiful, and exciting. But his storytelling skills didn’t match his vision....

Sign Up for "Writing Examples" and Learn From The Best Writing of All Time: https://www.writingexamples.com Ryan Holiday is one of the world’s most prolific writers. He’s published sixteen books, written a daily email newsletter every day for the past eight years, has 1.7 million YouTube subscribers, and runs his own creative agency. (Reciting that list is difficult enough to remember, let alone accomplishing all of those things). This conversation will get you off your butt as a writer....

Jerry Seinfeld taught me more about writing than all my English teachers combined. People forget that comedians aren’t just jokesters — they’re writers. And with 10 Emmy Awards, 3 Golden Globes, and a TV show that’s generated over three billion in revenue, it’s safe to say that Jerry Seinfeld is a dang good one.  In this episode, I share the top ten writing lessons I’ve learned from Jerry Seinfeld over the years. You’ll learn five lessons on getting your work done, and five lessons on making...

You may know Ted as a music historian, and the go-to expert on jazz. Or, you may know him as The Honest Broker on Substack. Either way, he’s the most erudite guest this show has ever seen. Ted gives a masterclass on the state of our culture at large. What’s up with our obsession with minimalism? Why do we value speed over beauty? Do we even realize that we’re distracting ourselves into oblivion? And, of course, what does this mean for us as writers? This episode zooms out to look at where...

Get ready to swap everything you know about business-writing for an unconventional approach that actually works.  Basecamp CEO Jason Fried is one of the world’s most successful software entrepreneurs. And he’s unique for the way he challenges the tenets of Silicon Valley startups.  He’s bold like Bezos, but relaxed like Buffett. He cares less about “rising-and-grinding” and more about an honest 40-hour work week. He never white-knuckles his ideas, but shares them freely with the world. As a...

From frustrated middle school teacher to Chief Evangelist at Synthesis School. From 46 email subscribers to 165,000. From hating writing to publishing her first book with a major publishing house: The Learning Game.  What made all of this possible for Ana Fabrega?  She unlearned how to write.  In this episode, Ana shares the seven writing principles you should unlearn if you want to fall in love with writing again and reach people with your ideas. Like Ana, your best ideas could have the...

This is business writing like you’ve never seen it before.  Sam Corcos is the founder of a $300 million company called Levels. He’s built a culture of intellectual rigor by hiring excellent writers and giving them time to think on paper. But don’t get it twisted — a successful “writing-first work culture” is far more than grammatically correct Slack messages and the occasional memo.  “95% of people would not be happy working in the culture that we’ve built. And the 5% who would be have been...

“I’m not writing for you.”  This was Paul’s response to a scathing critique that came early in his writing career. Since then, Paul’s book, The Pathless Path, has sold over 50,000 copies and has spurred thousands of writers to forge their own path forward — scathing critiques and all.  Writing isn’t about building the biggest readership possible. It’s about connecting with the readers who care. It’s about broadcasting a signal for the kinds of people you want to attract. And in this episode,...

There is an intrinsic interestingness inside of you. But, you’re probably suppressing it. Welcome to 96-minutes of learning how to use your interestingness to stand out online.  Speaking of standing out, Steph Smith: Hosts a16z, a top five technology podcast Taught herself to code and launched multiple websites that hit #1 on Product Hunt Sold over $220k in her book launch for Doing Content Right Grew The Hustle’s Trends product to millions And led HubSpot’s Creator Program. (Safe to...

Writing is thinking, which means it’s like lighter fluid for business growth.  Brie has played major roles at writing-rich companies like Stripe, and her expertise on writing-first culture is now used by giants like Amazon and Basecamp.  As she says: “Reality has a surprising amount of detail.” Writing illuminates all the interesting details worth pursuing. And as a result, companies who prioritize writing operate with impressive speed, intention, and rigor.  In this episode, Brie shares...

Paul Graham is one of the most successful writers and entrepreneurs in Silicon Valley. Sure, he sold a company to Yahoo and co-founded Y Combinator, which has created hundreds of billions of dollars in value. But more than that, Paul is a renowned essayist and his thoughts on what makes good writing are worth paying attention to. So, how has writing led to Paul Graham's success? I've deconstructed 11 of his best lessons and we're going to go through them one by one. Ultimately, you’ll learn...

Neil writes about all the icky, taboo things you’re not supposed to say out loud. As the author of ten New York Times Bestselling books, he’s built his career on getting celebrities like Rick Rubin, Kevin Hart, and Jenna Jameson to open up in a way that most writers are too afraid to do.  But don’t get it twisted — “being vulnerable” doesn’t mean “word-vomit your deepest, darkest secrets to the world.” It means sharing who you truly are in a way that’s interesting to other people.  In this...

Every year, 25 million people download Shaan’s podcast. Sure, he’s a brilliant entrepreneur, investor, and writer, but there’s one skill in particular that keeps Shaan’s audience coming back for more: storytelling.  And not the kind of storytelling that feels like an IQ contest. (I know you know what I mean.) Shaan tells stories that burst with aliveness, that make readers laugh out loud with joy or fall silent with understanding. And as a result, he’s built more than just a following; he’s...

Perhaps the best-kept secret of any writer is the ability to find inspiration in unconventional places. And that’s Michael Mauboussin in a nutshell. Investing, business, reading, writing, luck, skill — name a topic he’s passionate about, and he’s found a way to make money from it in his writing.  How? By subverting “The Curse of Knowledge.”  With his decades-long career on Wall Street, you’d think that reading Michael’s work would be like trying to learn Latin on the fly. But the opposite is...