Lenny's Newsletter

Lenny followed a pull where enjoyment and value to others overlapped. While exploring startup ideas after seven years at Airbnb, Lenny wrote up what he learned on the side. His first big Medium post, on lessons from Airbnb, was featured and shared inside the company, and a few later posts got the same warm reaction.

VC friend Lee Jacobs told him that doing something you enjoy that people also value is a rare Venn diagram, so he should double down; Michelle Rial added a missing circle, that he is good at it. None of his plans A to D (a startup, a first-PM job, a big-company PM role, consulting) involved writing, and he moved to Substack by tweeting that a weekly newsletter was an experiment.

Lenny's Podcast▶ 7:47

Prove a weekly cadence for nine months before adding a paywall. Lenny wrote every week for nine months, then reasoned by the Lindy effect that he could likely keep going nine more and added a paywall. It earned meaningful money about a month after launch.

COVID and doubts about his Airbnb stock made income urgent. The interview gives no subscriber, revenue or pricing figures beyond 1.2 million subscribers and "meaningful dollars". Quote: "I've been doing this every week for 9 months, which means I could probably do this for nine more months."

Lenny's Podcast▶ 8:54

Most posts come from practitioners doing the work, not pundits. Most of Lenny's posts are now guest posts in which a practitioner shares the single best thing they have learned in their career.

He holds that "the source of the best advice is from practitioners doing the thing for real, not just pontificating." Michelle's children's book written before she had kids was weaker, and the one written after raising a son worked.

Lenny's Podcast▶ 1:01:52

Each post gets about 50 passes before editors see it. Lenny reads a post, adds to it and improves it roughly 50 times. Then an editor, a copy editor and a designer work on it.

Michelle estimates her charts take at least five passes, probably closer to 100. Quote: "read through it, add to it, read through it, add to it, improve, improve, improve like 50 times".

Lenny's Podcast▶ 1:03:20

No full-time employees, so the business never becomes a job he hates. Lenny avoids full-time staff and works with a small team, including an engineer and editors. He is careful about what he commits to.

His warning: "you can create a job for yourself that you hate by doing things that people want you to do or by following opportunities that feel big." The tradeoff is that he now misses having a coworker.

Lenny's Podcast▶ 38:59

A weekly post and episode is a treadmill to plan around. A post and a podcast episode are due every week, which Lenny compares to the Indiana Jones boulder chasing him. He has kept the pace since 2019, about seven years, and the podcast is regularly a top 10 tech podcast.

His enthusiasm moves up and down and some weeks he would rather skip, but he says you can't survive "without being consistent and making it awesome every week." He has no answer for keeping the pace at 60, 70 or 100, and leans on mindset tools such as optimism from a University of Pennsylvania happiness course to manage the stress.

Lenny's Podcast▶ 11:44