How Writing Helped Jason Fried Build an 8-Figure Business | How I Write Podcast

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.
WRITE OF PASSAGE:
Want to learn more about the next class Write of Passage?
writeofpassage.com/
SPEAKER LINKS:
Website: world.hey.com/jason
Twitter: x.com/jasonfried
Medium: / jasonfried
Books: www.amazon.com/stores/author/...
PODCAST LINKS:
Website: writeofpassage.com/how-i-write
Apple: podcasts.apple.com/us/podcast...
Spotify: open.spotify.com/show/2DjMSbo...
TIMESTAMPS:
00:00:00 Introduction
00:01:30 Communication
00:03:30 Struggle and Flow
00:10:45 Guide to Internal Communication
00:12:45 Writing a book
00:14:40 Writing like a sprinter
00:22:00 Editing
00:24:00 Mistakes and imperfections
00:33:00 Time and schedule for writing
00:36:00 Bad writing in business and school
00:39:40 Founder letters and product demos
00:45:00 Writing has to be playful and fun
00:52:15 Email
01:01:30 Writing with movement (rhythm and bounce)
01:02:00 Writing class I would like to teach (Editing and Iteration)
01:08:00 Writing in hiring employees (Resumes and Cover letters)
01:10:00 Writing company updates (“Heart beats”)
01:15:00 Writing to customers (marketing copy)
01:22:30 Sharing your secrets (chef's recipes)
01:26:40 Loosen your grip (life, business, and writing)
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.

[@DavidPerellChannel]

Jason Fried is a legend of business. He’s published 4 books and 1,000s of blog posts and built a massively profitable software business his own way. How does he write? This interview is a 91-minute answer to that question. Here’s his method: 1. Don’t write, communicate. 2. If you’re writing and not feeling the flow, close the computer and walk away. Don’t struggle. 3. Jason’s best writing just flows out. There are no drafts. He gets the whole thing on paper in one sitting, then goes back to edit and play around with it. 4. How do you know when you’ve found a good idea? Well, you don’t know. You feel. You give in to your intuition, tune into your senses, and notice goosebumps. Follow those things. Good ideas are like slipstreams - they have their own effortless, accelerated pull. 5. You need a point of view. Something you stand for. Something you believe that others don’t. Something you see that others are blind to. That’s the writing that spreads and makes a difference. 6. Good writing has rhythm. It flows, it bounces, it brings the reader from one word to the next, then the next. 7. Focusing on attention at the expense of writing something of quality is a Faustian bargain. Jason says: “In the same way that sound isn’t music, traffic isn’t audience.” 8. If Jason could teach any writing class, he’d focus on distillation. He’d ask students to explain something in five pages, then one page, then one paragraph, then one sentence, then one snappy phrase. This would teach students to find the essence of what they’re saying. 9. Sometimes, it’s okay to be detached from your industry. Jason doesn’t read industry news and built his software company in Chicago, not Silicon Valley. That detachment gives him a point of view. 10. Murakami once wrote: “If you only read the books that everyone else is reading, you can only think what everyone else is thinking.” 11. Writing is the first filter he uses in the hiring process because he doesn’t look at resumes. Only cover letters. 12. Why is writing quality so important to him? He says: “Business writing isn’t about beauty or eloquence. It’s about clarity of thought. To write is to scale your thinking. And the better you write, the further your ideas spread, which is why good writers make the whole team smarter. When choosing between two people, hire the better writer.” 13. Jason’s tip for overcoming writer’s block: Don’t write, speak. Chances are, you won’t have a problem explaining what you’re trying to say out loud. So do that. Then write it down. 14. Writing prompt: Where are you the most unconventional in how you do things? Write about that. 15. Jason’s marketing strategy has been to share without expectation of return - books, blog posts, podcasts, design reviews, code reviews, and the ins-and-outs of how he runs his business. 16. Jason has time to write because he insists on an open calendar. That gives him time to walk, think, and follow his creative whims. He has no set writing schedule.

[@aliabdaal]

Absolutely phenomenal episode guys ❤❤

[@robleon]

That last segment with the drum analogy is exactly why I love Jason's work so much. Thanks so much for having him on the show!

[@jessehepburn]

Came here after watching his interview on My First Million. David is by far one of the best interviewers I’ve ever seen. Every guest looks like an absolute rockstar.

[@hindenburg2006]

37:20 I don't think a lot of companies have anything to SAY; they have a lot to SELL. THAT could be an entire essay by itself💚

[@joshmay9531]

This video should have 500k+ views. Great stuff David and Jason!

[@jamesowen7543]

Came across this channel a week or so ago... and it is eliiiiiite

[@StrategicStripping]

I really liked Jason's chill baseline of if it's too hard, start over, this shouldn't be miserable. lol... also that if you're having a hard time writing it, just say it, and then write that. I know what he means about when I go back to edit, I just make it longer and more complicated when I'm trying to make it clearer or easier to understand... I should have just stuck with V1, and sometimes deleting just isn't the answer. Starting over, is. Write to people, for people 👌🏼 I really love your podcast, David. You're a great host, ask great and well timed questions, you don't cut your guests off, your guests have all been awesome, super insightful, and the entire interview (of every one I've seen/heard) is pleasant to listen to the whole way through. Thanks for making these. By the way, this was a fun visual 19:41 lol

[@Met_Ethio]

Heavy hitters after heavy hitters. David doesn't miss.

[@naturehuman]

I'm 10 minutes in and this is already the best interview I've listened to in months.

[@jessehepburn]

Jason Fried’s bit about Basecamp’s long form writing filter 🔥 Heartbeats are a must-have in any large organization. Ideas should be judged on their merits alone - not politics.

[@leadgenjay]

Jason Fried's approach to business writing is refreshing

[@EcomCarl]

Jason insights on writing as an elegant, clear communication tool are invaluable. Embracing natural flow and the art of concise expression can significantly enhance our ability to connect and convey complex ideas effectively. 🖋

[@iAmWriting247]

Excited for this - Jason is great - watching now!

[@alexhartan]

Yess! I liked this before watching it. Jason is a LEGEND

[@abbeyalgiersPR]

What an awesome talk about writing- thank you! So helpful!

[@kahdri]

Amazing episode. It's always so enlightening to hear from Jason and his beliefs

[@sultanalshirah]

His book was my first audiobook to finish and repeat multiple times.

[@syedahafsa3062]

Name of the book?

[@sultanalshirah]

@@syedahafsa3062 Rework

[@sultanalshirah]

​@@syedahafsa3062Rework

[@Soccolich]

Nice, Jason is the best!

[@Torymorgan9]

Love a good football analogy 😊

[@JeevSen]

The sound is incredibly crisp and frankly, incredible, and yet I don't see any lapel mics. What did you use for microphones? Or was more post production?

[@DavidPerellChannel]

We have lapel mics under the shirt and overhead microphones that we clip out in post production… it’s a neat little trick

[@anaghnair]

Are you dropping the episode with sam altman soon?

[@coreys-dev]

My two coaches in one room! ha

[@oakwood3745]

Can anyone tell me what watch Jason is wearing? Looks like a white-dial speedmaster, but can't tell

[@37signals]

You nailed it, good eye. It's the new white dial Speedmaster. -JF

[@eshwarnag]

At around 1:15:00, I don’t know how many of you have observed the deep irony in what he says. He says for those struggle with writing, he would ask them to speak and they would do a better job and he agrees that most people can speak naturally and yet he claims that writing is more important?

[@yp5387]

22:55 Isn't it exact opposite of basecamp philosophy?

[@sultanalshirah]

First

[@sultanalshirah]

Bad choice of picture. He looks like a psychopath with that smile.

[@user-ck6sr2dq7o]

❤