When Lenny Rachitsky left Airbnb in the spring of 2019, he had a plan. He’d build a company. Seven years spent helping Airbnb grow — first as an engineer, then as the product lead running growth — had given him a thesis. He knew what it took to build things. He would build something.
The newsletter was not the plan.
The startup that ended at Airbnb
Rachitsky’s first company was Localmind: a mobile app built on top of Foursquare and Gowalla that let travelers message people checked in nearby to ask what was worth seeing, eating, or doing — a local intelligence layer over the era’s check-in services. He co-founded it with Beau Haugh in 2011, launched at South by Southwest, raised $600,000, and got the app featured regularly in the App Store. A seed round was next.
Then Airbnb called.
“I have this memory I’ll never forget,” he told First Round Review, “of sitting in an early Airbnb all-hands looking at a big ass Airbnb logo projected on the back wall, and thinking to myself ‘wait, how the hell did I end up at Airbnb?’”
The acquisition closed in December 2012. It wasn’t seamless: one of Localmind’s investors moved to block the deal, which was structured in all stock. Rachitsky and Haugh responded by threatening to quit Localmind and join Airbnb directly, which resolved the standoff. He arrived at the company still working out how he’d gotten there.
He stayed seven years. “Did I intend to stay there for seven years? Hells no,” he told investor Hunter Walk in 2020. “But man, it’s a tough place to leave.”
Project: Avoid Getting a Real Job
When he finally left, in spring 2019, he named the phase he was entering “Project: Avoid Getting a Real Job.” He gave himself six months. Plan A was a startup. Plan B was joining a company. Plan C was a larger company. He started looking at ideas.
What he did first was write. He distilled what seven years inside Airbnb’s product and growth function had taught him into an essay and put it on Medium. It found readers. He wrote another. Then another. He moved to Substack and, over the next ten months, published forty newsletters, each covering some dimension of building products, running growth, or managing the human side of startups. He published every week. He never missed one. All forty were free.
He wasn’t planning a media business. He was organizing what he knew and finding out who needed it. The audience that found him did so because other people forwarded the link.
April 2020
In April 2020, Rachitsky launched the paid tier of Lenny’s Newsletter: $150 per year, or $15 per month. By the end of 2020, the newsletter had 45,000 total subscribers and 3,300 paying members — roughly seven percent conversion. That translated to approximately $360,000 in annual recurring revenue.
His first year on Substack had generated $65,000. The first year with a paywall produced something north of $300,000.
For a former product lead at one of tech’s most valuable companies, the revenue was not the revealing detail. The revealing detail was the conversion rate. Seven percent of a newsletter audience choosing to pay for writing, in a period when free content was everywhere, meant the writing was doing something specific that those readers found hard to replicate elsewhere: clear, practiced, direct guidance from someone who had actually done the work.
The standard
Rachitsky has said he spends between five and one hundred hours on each newsletter issue, with that variance depending entirely on the topic. He reviews each piece roughly fifty times before it publishes.
That commitment is load-bearing. The growth engine for Lenny’s Newsletter, from the first free essay through the paid launch and beyond, was word of mouth — not referral programs, not advertising, not social media growth tactics. “My advice,” he told NBC in 2024, “is just stop tweeting and do the work.”
The observation is blunt but structurally accurate. A newsletter that people forward is a newsletter that compounds. The mechanism is slow and invisible until it isn’t.
The podcast he didn’t want to start
In 2022, three years after the newsletter launched, Rachitsky added a podcast. He was skeptical. Podcasts are difficult to discover organically, hard to clip and share, and production-intensive in ways that newsletters aren’t. The format is fundamentally less forwardable.
The show grew anyway. By January 2024, Lenny’s Podcast was generating more than $500,000 per year. The newsletter that month was generating more than $500,000 per year. CNBC reported that the two properties combined were bringing in more than $1 million annually, with 574,000 newsletter subscribers and more than 18,000 paying members.
One million
In March 2025, Lenny’s Newsletter crossed one million subscribers. By mid-2026, it stands at 1.2 million and holds the top spot among business newsletters on Substack — in the top four across all newsletter categories in the United States.
The business Rachitsky built is structurally unusual for a former startup founder and senior product leader: a media company, run lean, built on six years of not missing a week and spending a hundred hours on a piece when the topic demands it. No venture capital. No growth team. No paid acquisition.
What he did was start a company, get absorbed into a bigger one, stay too long by his own reckoning, and then leave to figure out what was next. What was next turned out to be forty free essays and the discipline to never stop writing.
The million readers came later. The discipline came first.
Related founders
- Pieter Levels Built a Flight Simulator in Three Hours. It Made $1M ARR in Seventeen Days. — a serial indie maker who built audience over a decade by shipping in public before his fastest launch ever.
- The Tweet to $10M: Yasser Elsaid Built Chatbase With No VC and No Sales Team — another founder who scaled to millions in ARR through product-led growth, no outside funding, and a single public post.
Quotes from Lenny Rachitsky are drawn from: his interview with investor Hunter Walk (hunterwalk.com, April 17, 2020); First Round Review, “Reluctantly Influential: Inside Lenny Rachitsky’s Demandingly Chill Life” (review.firstround.com), which is the source of the Airbnb all-hands memory and the Localmind investor standoff; and NBC/NBC Los Angeles, “42-year-old brings in more than $1 million a year from newsletter, podcast” (January 2024), source of the “stop tweeting” quote. Revenue and subscriber figures from: Substack, “How Lenny Rachitsky earned $65,000 in his first year of writing” (on.substack.com); CNBC, “Lenny Rachitsky brings in over $500,000 from his podcast — here’s how” (January 11, 2024); Growth In Reverse (growthinreverse.com) for paid subscriber counts. Localmind acquisition: TechCrunch, December 13, 2012. The one-million-subscriber milestone from Lenny’s own newsletter post, “1,000,000” (lennysnewsletter.com, March 2025).
