Lenny RachitskyHost of Lenny's Podcast | Author of Lenny's Newsletter

The turning point for my newsletter

13 Mar 2026 · 1 min

Watch on YouTube

0:38

In this YouTube monologue, Lenny Rachitsky recounts the pivotal moment that led him to launch his newsletter. He begins by describing his first viral Medium post about lessons from Airbnb, which was featured by Medium and shared company‑wide by Airbnb CEO Brian Chesky, giving him confidence that his writing resonated. After a few more successful Medium pieces, Lenny questions why he’s writing instead of focusing on his startup. A conversation with his friend Lee Jacobs provides the crucial insight: enjoying something that people value is rare, and it could be monetized. Lee encourages Lenny to double down on writing, which becomes the turning point that pushes Lenny to pursue a newsletter as a serious endeavor.

Chapters

The first thing I wrote on the internet did very well. It was this post on what I learned at Airbnb. Like Medium featured it, it went all over the place. Brian Chesky shared it with the whole company, he was so proud of what I shared. So that was a nice moment of like, maybe I have something to share. And then I wrote a few more things on Medium at this point, and there was more of just like, this is working, people seem to like it. Then I had a conversation with a friend, Lee Jacobs, because I was telling him, I don't know why I'm doing this. Why am I writing? This is like not a future. I should be focusing on the startup. And he's just like, You seem to be enjoying it. People seem to be liking it, which is very rare. How often do you enjoy something and people value it? And maybe there's a way to make money in the future. So his advice is just maybe pursue that and double down on that, and maybe it'll go somewhere.