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 years of h...
Apr 03, 2024•1 hr 7 min
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 the ...
Mar 29, 2024•1 hr
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 episode...
Mar 27, 2024•1 hr 22 min
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 built...
Mar 20, 2024•2 hr 49 min
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 true....
Mar 06, 2024•1 hr 8 min
Packy McCormick is proof that writing online can attract real-world opportunities you never dreamed of. He went from 20 Substack subscribers to a $40 million venture fund — and he’s still growing. In this episode, we dive into the three main “how’s” of Packy’s growth. First, he has a distinct, unforgettable style. His business-meets-memes newsletter, Not Boring, has amassed 220,000+ subscribers because his “funny finance guy” flair gives him an edge. Not to mention, it all started when he took t...
Feb 28, 2024•1 hr 23 min
Want to build influence with great ideas and simple writing? Look no further than Howard Marks. Most smart people use big words and plastic jargon to reinforce the barrier between themselves and “the common folk.” Howard, on the other hand, breaks down this barrier, and that’s why his ideas are so influential (and why he’s Warren Buffett’s favorite author). Ironically enough, simple writing is the hardest to master. Einstein once said that there are four types of intelligence: “bright, brilliant...
Feb 21, 2024•54 min
Amor Towles is our modern day F. Scott Fitzgerald. Sure, he’s a critically acclaimed, award-winning novelist (ever heard of “A Gentleman in Moscow”?) but not because he’s cracked the publishing algorithm. Rather than scheming how many books he can sell or how many critics he can impress, his #1 goal is to fulfill his covenant with his reader. “They’ve invested in my art, and I owe it to them.” Towles' work oozes sensory detail and psychological richness. While most writers would describe writing...
Feb 14, 2024•1 hr 15 min
Steven Johnson has studied LLM technology for over 35 years. His consensus? Large Language models and human creativity aren’t at odds. They’re at their best when they work in harmony. Johnson has written thirteen books, many of which explore how tools and technologies expand what humans are capable of and transform societies. He created NotebookLM to help writers use AI to supplement their creative process — not to replace their thinking, but to amplify it. In this episode, you’ll learn how to c...
Feb 07, 2024•2 hr 33 min
Chris Dixon is the perfect example of how learning in public can catapult you to success. Come learn how he went from writer to owner, and how you can, too. SPEAKER LINKS: Website: https://cdixon.org/ Twitter: https://twitter.com/cdixon Blog: https://cdixon.substack.com/subscribe Book: https://www.amazon.com/Read-Write-Own-Building-Internet/dp/0593731387 YouTube: https://www.youtube.com/channel/UCoAeFr1JnlHwQ1ex7WlWi-g WRITE OF PASSAGE: Want to learn more about the next class Write of Passage? h...
Jan 31, 2024•1 hr 28 min
It’s the start of 2024 and to celebrate I thought I’d run through some of the best lessons I’ve picked up over the last 12 months. This past year has had over 20 episodes produced so there was a lot to choose from but I ended up settling on 8 insights from some of my favorite conversations both inside and outside of the podcast. Expect to learn how Tim Ferriss sets an extremely high/low quality bar, why Marc Andreessen uses a barbell approach to consume information, Kevin Kelly’s reason to be th...
Jan 24, 2024•1 hr 1 min
Tiago grew up reading in Barnes and Noble — up to six hours at a time! Now, his bestselling book, Building a Second Brain, is the perfect combination of his favorite genres: self-development, business, and tech. Come learn how Tiago has helped thousands of people unlock their creative potential. SPEAKER LINKS: Website: https://fortelabs.com/ YouTube: https://www.youtube.com/@TiagoForte Twitter: https://twitter.com/fortelabs Blog: https://fortelabs.com/blog/ Book: https://www.buildingasecondbrain...
Jan 10, 2024•1 hr 3 min
Tim Urban used to hate writing because he thought it was boring. Now, he has 600,000+ newsletter subscribers, 811,000+ Twitter followers, and one of the most unforgettable (and hilarious) writing styles on the Internet. Come learn how to make your writing fun to read and fun to write. SPEAKER LINKS: Website & Newsletter: https://waitbutwhy.com/ Twitter: https://twitter.com/waitbutwhy Book: https://waitbutwhy.com/whatsourproblem WRITE OF PASSAGE: Want to learn more about the next class Write of P...
Jan 03, 2024•1 hr 12 min
Tim Ferriss has built one of the most lucrative personal brands on the Internet: 2,000,000 newsletter subscribers, 5 #1 New York Times Bestselling books, and 900 million podcast downloads. Come learn his top writing tactics, routines, and habits! SPEAKER LINKS: Website: https://tim.blog/ Newsletter: https://go.tim.blog/5-bullet-friday-1/ Books: https://tim.blog/tim-ferriss-books/ Podcast: https://tim.blog/podcast/ Twitter: https://twitter.com/tferriss WRITE OF PASSAGE: Want to learn more about t...
Dec 27, 2023•1 hr 29 min
Sahil Bloom once believed working in finance was the only way to make money; then, he started writing online and proved himself wrong. Come learn how he turned Twitter threads into 1 million followers by writing with soul. SPEAKER LINKS: Website: https://www.sahilbloom.com Twitter: https://twitter.com/SahilBloom Newsletter: https://www.sahilbloom.com/newsletter WRITE OF PASSAGE: Want to learn more about the next class Write of Passage? Click here: https://take.writeofpassage.school/writing-sprin...
Dec 20, 2023•1 hr 25 min
Byrne Hobart has a Substack following of over 50,000 subscribers, consisting of some of the smartest people in Silicon Valley — startup founders, venture capitalists, hedge fund managers, you name it. Come learn how he produces high-density, high-insight ideas so consistently. SPEAKER LINKS: Newsletter: https://www.thediff.co/ Twitter: https://twitter.com/ByrneHobart LinkedIn: https://www.linkedin.com/in/byrnehobart WRITE OF PASSAGE: Want to learn more about the next class Write of Passage? Clic...
Dec 13, 2023•1 hr 13 min
From making his first dollar online at 12 years-old to raking in $4,000,000 a year, Ali Abdaal is not your average online creator. And his advice on how to “make it” online is not so average, either. SPEAKER LINKS: Website: https://aliabdaal.com/ YouTube: https://www.youtube.com/@aliabdaal Twitter: https://twitter.com/AliAbdaal Instagram: https://www.instagram.com/aliabdaal Book: https://www.feelgoodproductivity.com WRITE OF PASSAGE: Want to learn more about the next class Write of Passage? Clic...
Dec 06, 2023•1 hr 11 min
Come learn how Chamath Palihapitiya, tech billionaire and Silicon Valley icon, breathes life into his ideas — and how you can, too. SPEAKER LINKS: Website: https://www.socialcapital.com/ Twitter: https://twitter.com/chamath Annual Letters: https://www.socialcapital.com/annual-letters Newsletter: https://chamath.substack.com/ WRITE OF PASSAGE: Want to learn more about the next class Write of Passage? https://take.writeofpassage.school/writing-sprints PODCAST LINKS: Website: https://writeofpassage...
Nov 29, 2023•47 min
Steven Pressfield waded through 27 years of Resistance so you don’t have to — come learn his best practices to creating your best work. SPEAKER LINKS: Website: https://stevenpressfield.com/ Instagram: https://www.instagram.com/steven_pressfield Books: https://stevenpressfield.com/books/ WRITE OF PASSAGE: Want to learn more about the next class Write of Passage? Click here: https://take.writeofpassage.school/writing-sprints PODCAST LINKS: Website: https://writeofpassage.school/how-i-write/ Apple:...
Nov 22, 2023•1 hr 26 min
Learn how Garry Tan, CEO of Y Combinator, wrote his way to success in the startup world — and how you can, too. SPEAKER LINKS: Website: https://www.ycombinator.com/people/garry-tan Twitter: https://twitter.com/garrytan Instagram: https://www.instagram.com/garrytan/ Blog: https://blog.garrytan.com/ YouTube: https://www.youtube.com/@GarryTan Linkedin: https://www.linkedin.com/in/garrytan WRITE OF PASSAGE: Want to learn more about the next class Write of Passage? Click here: https://take.writeofpas...
Nov 15, 2023•1 hr
When people ask me what good online writing looks like, I point them to Morgan Housel. Why? He takes dry financial concepts and breathes life into them with captivating stories. And he’s been doing it for a decade and a half. Before Morgan wrote “The Psychology of Money” — one of the world’s most popular finance books that’s now sold over 4 million copies — he spent years as a prolific writer. He wrote 2-4 articles a day when he worked at Motley Fool (3,500 in total). Then, he wrote a bunch more...
Nov 06, 2023•2 hr 3 min
Mark Manson’s success as a writer stems from one central idea: “What feels like play?” After his dating blog took off in 2012, Mark started writing about all the things that excited him: psychology, personal development, and “self-help for people who hate self-help.” His breakout book, “The Subtle Art of Not Giving a F*ck,” was the #1 most read nonfiction book worldwide in 2017 (and I swear I saw it on the front table of every airport I went to). Mark was once described as “the local drunk who s...
Nov 01, 2023•2 hr 30 min
Lenny writes one of the top five business newsletters on Substack — which has amassed over 500,000 subscribers. He hosts a podcast that makes him more money than he made in corporate America. And he’s built a raving X audience of over 188,000. No training. No ego. And to top it all off, he writes in one of the most oversaturated markets on the Internet: product management. How does he do it? After his first Substack post went viral, “What Seven Years at Airbnb Taught Me About Building a Business...
Oct 25, 2023•1 hr 23 min
Riva Tez is one of the freest writers I know. It’s as if the boundaries of conventional thinking don’t apply to her. She’s allergic to dogma and passionate about questioning the taboos of our time, and her obsessive research gene has given her a knack for stumbling upon forgotten and under-explored ideas. She’s a singular human being. Part of her brilliance is the way she combines her love for Rilke’s poetry with an interest in philosophy, theology, and consciousness. In all three areas, she goe...
Oct 18, 2023•1 hr 25 min
Sam is a master copywriter and business builder. If there was ever somebody who knows how to turn online writing into cash, Sam is it. In this episode, Sam shows how you can sell at scale and where to find the opportunities in the business of writing. We’ll teach you how to think through headlines, find content for your own writing, and torch the internet with your ideas. Sam started in the early days of email newsletters and he was a master of writing viral content. He tells the story about pla...
Oct 11, 2023•1 hr 11 min
Marc Andreessen deserves a place on the Mount Rushmore of Silicon Valley. His presence in the tech space is unprecedented and he's one of the most prolific investors. The world of online writing is in debt to him. He co-founded Netscape, where he created the first popular web browser. He invented the tweetstorm, and has helped form the internet. He coined the idea “software is eating the world”, which has defined humanity's evolution over the last decade. Marc isn’t just a mad man creator. He’s ...
Oct 04, 2023•1 hr 18 min
How do you create intimacy and connection with readers? While some writers have a way of letting you inside their mind, Ava (@noampomsky) has a way of letting you inside her heart. There's an intimacy about her writing - an honesty, a tenderness, a contemplative-ness, a sense of connection that shows up in her work and it's what makes her unique. Ava sees writing as a distinct form of consciousness. This process of continually excavating your mind to find out what you think and then eventually y...
Sep 28, 2023•1 hr 18 min
It’s hard to capture in words the love and creativity that Derek Sivers brings to his work. He describes himself as a “monomaniac, introvert, and slow thinker.” But those words just reveal his humility. Derek’s work has charmed millions — from his early days as a professional musician and circus performer, to founding CD Baby, writing fan favorites like Anything You Want and taking the stage at TED. In this conversation, Derek shares how he finds his best ideas, why he plans to publish a “posthu...
Sep 20, 2023•1 hr 12 min
Kevin Kelly is one of the most important tech writers of the last half century. Kevin started as the publisher and editor of the Whole Earth Catalog, which was one of Steve Jobs’ favorite publications. After being mentored by Stewart Brand, he started writing books and magazine pieces before cofounding Wired Magazine. He has since become a prolific author - writing one feature article for Wired Magazine every year, and writing numerous bestselling books. The man is full of mysteries. Kevin write...
Sep 13, 2023•1 hr 18 min
Lulu Cheng Meservey gives a masterclass on non-boring corporate communications, Korean pop culture, and religious fanaticism. Lulu shares what she’s learned running comms for startups, decoding cultural erogenous zones, and crafting impactful messages in 280 characters or less. Whether you're a writer, a communications professional, or simply curious about the intersection of K-POP and Internet whackos, this podcast is a window into modern communication. Lulu is currently the Executive Vice Pres...
Sep 06, 2023•1 hr 11 min
