How I Write

“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, you’ll learn how to find these people. 

Paul shares his story from corporate cog to free-spirited wanderer, from blogger to author, from intellectual loner to leader of a thousands-strong community. Flow. Space. Surprise. The joy of finding out. These are just a few phrases Paul uses to describe how he writes. 

So, what about you? Who are you writing for? If you’re ready to write with a heart on fire and find the people who care, this episode is for you. 

SPEAKER LINKS:

Website: https://pmillerd.com

Twitter:  https://x.com/p_millerd

Instagram: https://www.instagram.com/pathlesspaul

Substack: https://substack.com/@paulmillerd

Linkedin:  https://www.linkedin.com/in/paulmillerd/

Book: https://amzn.to/4aBxEUZ 

WRITE OF PASSAGE: 

Want to learn more about the next class Write of Passage?

https://writeofpassage.com

PODCAST LINKS: 

Website: https://writeofpassage.com/how-i-write

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

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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:

(Safe to say that she knows what she’s talking about.) And now, Steph reveals everything she’s learned about creating unforgettable work on the Internet. 

Millions of people mirror what you do — your job, hobbies, routines — but how you do it is another story. Come learn how to follow your compass of interestingness and stand out online.

SPEAKER LINKS: 

Website: https://stephsmith.io/

Twitter: https://twitter.com/stephsmithio

Blog: https://blog.stephsmith.io/

Linkedin: https://www.linkedin.com/in/stephaniesmith93

WRITE OF PASSAGE: 

Want to learn more about the next class Write of Passage?

Click here: https://writeofpassage.com

PODCAST LINKS: 

Website: https://writeofpassage.school/how-i-write/

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

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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 hard-won wisdom to expose how great writing sets companies apart. She explores the balance of writing vs. taking action; she breaks down the editing process better than a modern-day Maxwell Perkins; and she sheds light on the secret to great writing: your zone of obsession. 

If you want to learn how to do the best writing of your life, and grow your company while you’re at it, this episode is for you. 

SPEAKER LINKS: 

Website: https://www.briewolfson.com/

Twitter: https://twitter.com/zebriez

Stripe Press: https://press.stripe.com/

WRITE OF PASSAGE: 

Want to learn more about the next class Write of Passage?

Click here: https://writeofpassage.com/

PODCAST LINKS: 

Website: https://writeofpassage.com/how-i-write

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

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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 writing secrets behind this mega-successful investor, how he engages and delights his audience, and how you can, too.

Also, if you listen until the end, I have an unreleased goodie in here about what Sam Altman learned from Paul Graham. And I'm not going to share that anywhere else.

LINKS FOR PAUL GRAHAM: 

Website: https://www.paulgraham.com/

Twitter: https://twitter.com/paulg

Book: https://www.paulgraham.com/books.html

WRITE OF PASSAGE: 

Want to learn more about the next class Write of Passage?

Click here: https://writeofpassage.com/

PODCAST LINKS: 

Website: https://writeofpassage.com/how-i-write

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

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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, Neil reveals how to be vulnerable in your work, the right way. He breaks down story structures that hook your reader. He reveals how to cultivate your life to support your writing. And he shows you how to say things in public that most people would be too scared to share with their closest friends. 

If you’re scared of sharing your work in public, this episode is for you. Come learn how to synthesize your vulnerability in a way that resonates with other people.

SPEAKER LINKS: 

Website: https://www.neilstrauss.com/

Twitter: https://twitter.com/neilstrauss

Instagram: https://www.instagram.com/neil_strauss

Books: https://www.amazon.com/Neil-Strauss/e/B001H6NT1I

WRITE OF PASSAGE: 

Want to learn more about the next class Write of Passage?

Click here: https://writeofpassage.com/enroll

PODCAST LINKS: 

Website: https://writeofpassage.school/how-i-write/

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

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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 a fandom. 

In this episode, Shaan reveals every framework he knows for telling stories so well they make your reader go, “Wait, how did they do that?”. And I mean, every framework. You won’t find this in the ole’ self-help aisle. Plus, he shows you exactly how to do it. We deconstruct everything from popular movies to business origin stories to viral Twitter threads. 

Stories are the #1 way to grab readers’ attention, get them to like you, and ultimately, turn them into fans. And this episode is a masterclass on how to do it.

WRITE OF PASSAGE: 

Website & Newsletter: https://www.shaanpuri.com/

Twitter: https://twitter.com/ShaanVP

Linkedin: https://www.linkedin.com/in/shaanpuri

WRITE OF PASSAGE: 

Want to learn more about the next class Write of Passage?

Click here: https://writeofpassage.com/

PODCAST LINKS: 

Website: https://writeofpassage.school/how-i-write/

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

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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. 

“I put my arm around the reader, and we gaze off into the world and say, “Let’s talk about what we see. Let’s make this concrete and interesting.” 

No stuffy professionalism. No robotic jargon. While many of us writers see the ignorance of a reader as a handicap, Michael sees it as an opportunity. And as a result, he’s become a billboard for how to build a career around who you truly are and what you’re actually interested in. 

In this episode, you’ll learn how to do the same. Come learn tactical writing and life instruction from one of Wall Street’s best and brightest. 

SPEAKER LINKS: 

Website: https://www.michaelmauboussin.com/

Books: https://www.michaelmauboussin.com/books

Twitter: https://twitter.com/mjmauboussin

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/

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

Learn more about your ad choices. Visit megaphone.fm/adchoices

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 the first-ever cohort of Write of Passage. (I may be biased, but seriously, that’s when it started.)

Next, Packy shares his domain expertise. He sees writing and investing as the perfect one-two punch. His goal? Share what he knows, and make a behind-the-scenes world accessible to the average audience.

And finally, Packy adds value to his readers. Relentlessly. Not by telling them what to think, but by trying to change the way they think. In a world filled with Beta content — cheap entertainment that disappears in 24 hours — Packy creates Alpha content — quality work that has long-term relevance.

Style. Expertise. Value. This is just a sneak-peek into our conversation. If you want to find your distinctiveness in a modern digital world, this episode is for you.

SPEAKER LINKS:

Website: https://www.packym.com/

Twitter: https://twitter.com/packyM

Newsletter: https://www.notboring.co/

WRITE OF PASSAGE:

Want to learn more about the next class Write of Passage?

https://writeofpassage.com/

PODCAST LINKS:

Website: https://writeofpassage.school/how-i-write/

Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

Learn more about your ad choices. Visit megaphone.fm/adchoices

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, genius, and simple.” In this episode, you’ll hear how Howard turns decades of investment expertise into clear, simple language. 

You’ll learn: 

Ultimately, you’ll learn how this billionaire investor shares his ideas in a way that engages and delights his audience, and how you can, too.

SPEAKER LINKS: 

Website: https://www.oaktreecapital.com/about/leadership/bio/howard-marks

Twitter: https://twitter.com/howardmarksbook

Books: https://www.amazon.com/Howard-Marks/e/B004LE5B00

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/

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

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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 as “creative” or “free-spirited,” he describes it as “accurate” and “careful.” Every sentence he writes serves a larger truth. In this episode, Towles gives one of the most detailed breakdowns of his writing process that we’ve had so far on How I Write. 

You’ll learn the step-by-step process for how Towles drafts each novel; specifically, how outlining your work can free up your creative, poetic side. You’ll learn how to write descriptively — without bogging down your reader in indulgent details. You’ll learn how to master craft through repetition; how to approach your first draft versus your second; how to influence your writing with reading; and how to create art that serves a broader purpose. 

Ultimately, you’ll learn how to tell exceptional stories from one of today's most exceptional storytellers.

SPEAKER LINKS: 

Website: https://www.amortowles.com/

Twitter: https://twitter.com/amortowles

Books: https://www.amazon.com/stores/Amor-Towles/author/B004MW8MG6

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: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470

Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv

YouTube: https://www.youtube.com/@DavidPerellChannel/videos

ABOUT THE HOST: 

I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible.

Learn more about your ad choices. Visit megaphone.fm/adchoices