Lenny Rachitsky's Advice on Writing: How an Ex-Airbnb PM Built the Top Product Newsletter

Lenny Rachitsky left Airbnb in 2019 with no plan to become a writer. He started jotting down lessons from seven years of product management. Those notes became a Medium post. The Medium post became a newsletter. The newsletter became the number one paid business publication on Substack, with over 500,000 subscribers.

He did not set out to build a media business. He set out to organize what he knew. The business followed.

His process draws from a Substack growth profile, a Growth In Reverse analysis, and a Userpilot overview of his work.

The Accidental Newsletter

Rachitsky wrote his first substantial piece in Evernote. It was called "What Seven Years at Airbnb Taught Me About Building a Business." He published it on Medium. The CEO of Airbnb shared it internally. Medium featured it. It became one of the top posts on the platform.

His friend Andrew Chen told him something that changed his trajectory: it is rare to find something you love doing that the market also loves. Double down on it.

Rachitsky moved to Substack in June 2020. He published free content for ten months before launching a paid tier. During those ten months he confirmed two things. First, that he genuinely enjoyed the work. Second, that he had enough ideas to sustain it long-term. Both conditions had to be true. A paid newsletter you hate writing is just a bad job.

Ten to One Hundred Hours Per Post

Each post takes ten, twenty, or sometimes over a hundred hours. Rachitsky takes multiple research and revision passes on every piece. He reads through his posts ten, twenty, thirty times, looking for things to tweak, simplify, cut, or rearrange. "Until it's just like, okay, this is great. I don't know what else I could do."

He does not write drafts in one sitting. He keeps adding to the piece, flushing out bullet points over multiple sessions. Each time he returns, he reads from the top looking for friction - where does he get caught, where does something not quite work. His friend describes this as "writing friction." The goal is the ultimate efficiency between what you learned and how quickly you can get it into the reader's brain.

He also employs a copy editor at roughly a hundred dollars per post who catches about a hundred errors every time - commas, grammar, capitalization, pronouns. "No matter how much I think it's done, there's like a hundred things."

This investment per post is unusual in newsletter writing. Most newsletters optimize for publishing frequency. Rachitsky optimizes for depth. The result is that readers treat each post as a reference document, bookmarking it and returning to it months later.

Two Articles Drive Half the Growth

Rachitsky discovered that 50% of his email subscribers came from just two major posts. The other 50% came from consistent weekly publishing. Two posts out of hundreds drove half his audience growth.

The implication is clear. You need both. Weekly publishing builds the base. Occasional epic deep dives create growth spikes. Rachitsky's advice: "Keep writing great stuff every week, and then work on something epic in the background."

He does not know in advance which posts will be the epic ones. The marketplace piece that took months of interviews with 25 industry leaders became a growth driver. But so did a simpler post that just happened to capture something people needed at the right moment.

Jobs to Be Done for Readers

Rachitsky thinks about his newsletter through the jobs-to-be-done framework. People read not because of the topic but because they have a job they want done: get better at building product, grow their product, accelerate their career. If he does that better than anything else, people gravitate toward it.

He thinks of a mental puzzle board of every question founders and product teams have. His job is to fill in each puzzle piece. "Until I can fill that whole puzzle board, I have stuff to write about."

This framing shapes everything. Introductions stay short because readers want the answer, not a preamble. Signal to noise stays high because that is the job. He will open with a chart that contains the entire answer, then say: if you want to keep reading, here is how he got there with all the quotes and stories.

Framework-Driven Writing

Rachitsky's posts follow a consistent structure. A reader question. Research across multiple companies. A synthesized framework. Actionable takeaways.

This is product thinking applied to writing. Identify the user's problem. Research solutions. Synthesize findings into something usable. Ship it.

The framework approach differentiates him from opinion-driven writers. Morgan Housel uses stories to convey financial wisdom. Rachitsky uses frameworks to convey product wisdom. Stories make you feel. Frameworks make you act. Both are valuable.

His three rules for every post: only discuss topics where he has genuine expertise or has consulted experts, offer novel perspectives rather than rehashing existing content, and make everything actionable and concrete.

Guest Posts as Growth Levers

Rachitsky grew his early audience through guest posts on established newsletters, including Andrew Chen's publication and First Round Review. Each guest post generated roughly 500 new subscribers.

"Guest posts are effective because they allow you to get in front of your potential audience in a really easy way."

The key is writing for publications whose readers overlap with your target audience. A guest post on a general interest blog brings general interest readers. A guest post on a product management blog brings product managers. Rachitsky was precise about where he placed his work.

Curiosity Over Optimization

As each Tuesday approaches, Rachitsky picks the topic he is most excited to write about that week. Not the topic with the highest SEO potential. Not the topic most likely to go viral. The topic that genuinely interests him.

"Optimizing for my own curiosity versus what people want always leads to the best stuff."

This sounds counterintuitive for someone running a business. But the logic holds. Writing driven by genuine curiosity produces better work. Better work attracts more readers. More readers grow the business. The shortcut through forced topic selection produces mediocre posts that damage the brand.

The Advice Column Model

Rachitsky built his newsletter as an advice column for product managers, growth professionals, and people managers. Readers submit questions. He researches answers.

This model solves the hardest problem in newsletter writing: what to write about. The audience tells you. When the same question appears three times from different readers, that is a signal. The demand is pre-validated before you write a word.

The model also builds loyalty. Readers who submit questions feel invested in the newsletter. They become evangelists because they contributed to creating the content.

No Meetings Until 3 PM

Rachitsky protects his creative time with a strict schedule: no meetings before 3 PM. The morning and early afternoon are for thinking, researching, and writing. After three, he takes calls for angel investing, podcast interviews, and catching up with friends. Even after three, he tries to avoid meetings entirely.

He attributes this to Naval Ravikant's observation that as you become successful, you have less time to do the thing that made you successful. Networking events, panels, talks - they all pull you away from the writing. Rachitsky says no to almost everything by default. He has policies, templates, and excuses ready. "I just had a kid" is the current one. The goal is to keep writing every week for the rest of his life, and that requires saying no to everything else.

Patience Is the Strategy

"This is growing. It's not a 'one day and you're done' kind of thing. This is an ongoing thing, so just keep at it."

Rachitsky earned $65,000 in his first year of writing. That is far less than his Airbnb compensation. The financial return was not the point in year one. Year one was about proving the concept, building the habit, and confirming that the work was sustainable.

The overnight success narrative is always a lie. Behind every large newsletter is a year of writing to a small audience that did not seem to be growing.

Key Takeaways

• Start with what you know. Rachitsky's first hit was simply what he learned at Airbnb.
• Invest deeply in each post. Ten to one hundred hours per piece creates reference-quality content.
• Write consistent weekly posts and occasional epic deep dives. Both drive growth differently.
• Use frameworks, not just opinions. Actionable structure compounds trust.
• Guest post on publications where your target readers already are.
• Follow your curiosity. It produces better work than optimization.
• Let your audience tell you what to write about. The advice column model pre-validates demand.
• Be patient. Nonlinear growth takes time to ignite.

Rachitsky proves that a product manager with deep expertise, genuine curiosity, and patience can build a newsletter that exceeds any corporate salary. No media background. No writing degree. Just someone who organized what he knew and shared it consistently.

Sources: Rachitsky's Substack growth profile, Growth In Reverse analysis, and Userpilot overview. Athens is an AI writing editor.