
How I Write
David Perell
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Top 10 How I Write Episodes
Goodpods has curated a list of the 10 best How I Write episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to How I Write for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite How I Write episode by adding your comments to the episode page.

11/15/23 • 59 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.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
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2 Listeners

10/25/23 • 83 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”, Lenny saw the positive impact that his ideas had on his readers. He became obsessed with adding value. His motto?
“There’s always room for better content.”
In an age of cheap, viral-hungry clickbait, Lenny’s quality bar is through the stratosphere. He spends hours researching and revising. He takes ten, twenty, thirty passes on every piece he writes. He’s hyper-focused on adding value. And his audience loves it. His commitment to quality catapults his content above the noise.
In this episode, you’ll see inside Lenny’s process. He opens up about creating high-signal content; following what energizes him; balancing storytelling with practicality; protecting his writing schedule; and above all, rising above the noise.
Twitter: https://twitter.com/lennysan
Website: https://www.lennyrachitsky.com
Newsletter: https://www.lennysnewsletter.com
Podcast: https://www.lennyspodcast.com
Want to learn more about the next course with Write of Passage?
Click here: https://writeofpassage.school/hiw
Want to learn more about How I Write?
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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04/17/24 • 66 min
“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?
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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Derek Sivers: No Wasted Words
How I Write
09/20/23 • 71 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 “posthumous autobiography,” and why life is not a problem to be solved but a paradox to be experienced.
Website: sive.rs
Twitter: @sivers
Books:
How to Live: 27 Conflicting Answers and One Weird Conclusion
Anything You Want: 40 Lessons for a New Kind of Entrepreneur
Hell Yeah or No: What’s Worth Doing
Want to learn more about the next cohort with Write of Passage?
Click here: https://writeofpassage.school/hiw
Want to learn more about How I Write?
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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08/30/23 • 66 min
Derek Thompson weaves together ideas from all over the place — economics, public policy, sports, and even pop culture. His writing is a breath of fresh air in a world of cookie cutter Internet content. Where other click-hungry journalists have caved to antagonistic practices, Derek’s writing is cool and charitable. And it’s also poetic. With a background in theater, he draws inspiration from the likes of literature and playwrights. This conversation will appeal to anybody who wants to write more elegantly, deal with critics, and master the art of the non-fiction story.
Twitter: https://twitter.com/dkthomp
Website: https://www.theatlantic.com/author/derek-thompson/
Podcast: https://podcasts.apple.com/us/podcast/plain-english-with-derek-thompson/id1594471023
Books: Hit Makers: How to Succeed in an Age of Distraction - https://a.co/d/3yAif4H
Want to learn more about the next cohort with Write of Passage?
Click here: https://writeofpassage.school/hiw
Want to learn more about How I Write?
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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Riva Tez: Becoming A Free Thinker
How I Write
10/18/23 • 84 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 goes right after dogma — and by asking the questions that only she can ask, she finds the answers that only she can find.
In a world of people who are obsessed with optimization, Riva is passionately unoptimized; in a culture of people who are obsessed with the news, Riva has cut out almost all the contemporary noise from Netflix to the New York Times.
If you feel constrained in your writing or thinking, this episode is for you. An hour with Riva will free you from the trappings of your mind, unleash your creative spirit, and lift your head up to a divine calling.
Twitter: @rivatez
Medium: Riva-Melissa Tez
Article: Walking with Nietzche
Forbes: 30 Under 30 Profile
Want to learn more about the next course with Write of Passage?
Click here: https://writeofpassage.school/hiw
Want to learn more about How I Write?
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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09/13/23 • 77 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 writes abundantly but types very slowly. He writes often but calls himself a reluctant writer. He constantly explores new ideas but actually likes editing more than writing.
Rare is the opportunity to sit down with the master who has decades of experience as a writer. This episode is a peek behind the curtain.
SPEAKER LINKS:
Website: https://kk.org
Twitter: https://twitter.com/kevin2kelly
Latest Book: "Excellent Advice for Living": https://a.co/d/3nYau0X
Want to learn more about the next cohort with Write of Passage?
Click here: https://writeofpassage.school/hiw
Want to learn more about How I Write?
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

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05/22/24 • 91 min
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 result, he’s transformed how Internet businesses are being built.
And it all starts with — you guessed it — getting his best ideas on the page.
His founder letters stand out (and they’re his favorite thing to write). Whenever he announces a new product, he releases a letter that does three things: builds a devoted fanbase, ramps up excitement, and sheds light on the purpose behind his products. And in this episode, you’ll learn exactly how he does it.
You’ll learn specific business-writing techniques: from storytelling to structure to word choice. You’ll learn how to find your flow, make writing easier, and use writing to start doing things in the world.
SPEAKER LINKS:
Website: https://world.hey.com/jason
Twitter: https://x.com/jasonfried
Medium: https://medium.com/@jasonfried
Books: https://www.amazon.com/stores/author/B002MQ13PQ
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
Learn more about your ad choices. Visit megaphone.fm/adchoices

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03/20/24 • 108 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 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
Learn more about your ad choices. Visit megaphone.fm/adchoices

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10/11/23 • 71 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 plagiarizing his way onto Amazon’s bestseller list by looking at the intersection of romantic comedies, werewolves, and the Twilight Series. He combined many stories, self published his own book, sued by a publisher for plagiarizing, and ended up exploding on the self-publishing Reddit forum — all of which led to 1000s of new subscribers for his newsletter.
Since then, his success continues to multiply. First, by selling “The Hustle” for eight-figures to HubSpot. Then, by growing “My First Million” into one of the top ten business podcasts in the world. And now, he recently launched a company called Hampton.
One thing that stands out with Sam is how good he is at colloquial copywriting. His writing sells because it sounds like how people actually talk. First he builds trust with people. Then they open up their wallets. He gets people to open up their wallets by building trust with them very fast through writing. In this episode, he shows exactly how to do that.
Twitter: https://twitter.com/thesamparr
Website: https://www.Joinhampton.com
Podcast: https://www.mfmpod.com
Want to learn more about the next course with Write of Passage?
Click here: https://writeofpassage.school/hiw
Want to learn more about How I Write?
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
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FAQ
How many episodes does How I Write have?
How I Write currently has 72 episodes available.
What topics does How I Write cover?
The podcast is about Podcasts, Books, Education and Arts.
What is the most popular episode on How I Write?
The episode title 'Garry Tan: Y Combinator CEO - The Key To Writing For Startups and Entrepreneurs' is the most popular.
What is the average episode length on How I Write?
The average episode length on How I Write is 79 minutes.
How often are episodes of How I Write released?
Episodes of How I Write are typically released every 7 days.
When was the first episode of How I Write?
The first episode of How I Write was released on Aug 20, 2023.
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