Medium

Lenny's first Medium post gave him the signal to keep writing. His first big post on what he learned at Airbnb was featured on Medium and spread widely, and a few more posts got the same warm reaction. That response led to a newsletter that now has 1.2 million subscribers.

He kept writing while exploring startup ideas, even though people told him you can't make money writing online. His friend Lee Jacobs, a VC, told him that enjoying something that others also value is a rare Venn diagram, so he should double down: "you seem to be enjoying it. People seem to be liking it which is very rare that ven diagram of things".

Lenny's Podcast▶ 7:47