In early 2019, after seven years as one of Airbnb’s first product managers, Lenny Rachitsky quit to go and find his next startup.
Writing wasn’t on the list. He’d looked at what was already online and decided “it’s too late, everything’s out there.”
So the newsletter he started that spring was a side project, something to keep him busy while the real idea showed up.
Today that side project is the biggest business newsletter on Substack, with 1.2 million subscribers.
He turns away 98 percent of the CEOs who ask to come on his show, has never run an ad in the newsletter, and has never hired a full-time employee.
He was also told he’d make millions if he took a real job again, and said no.
And yet the last time he gave a number on earnings, in 2024, the newsletter and the podcast he built beside it were each clearing half a million dollars a year.
He still doesn’t believe he’s the expert, and his whole journey traces back to an email he sent thirty friends in 2019, with one request: slap me if I ever say I’ll do this full-time.
Forty Free Issues And a Price That Was More Than Netflix
In the spring of 2019, Lenny Rachitsky opened a note in Evernote and started typing out what seven years at Airbnb had taught him about building a business.
He’d landed there in 2012 when Airbnb bought his first startup, a location app he now calls “a terrible business idea.”
The note became a Medium post, the post hit the front page, and Brian Chesky forwarded it to the whole company.
That was the first sign that a shy engineer, who’d needed a psychedelic weekend in Joshua Tree to work up the nerve to publish anything, might have something people wanted.
His plan for the year still ran startup first, advising second (and writing nowhere), so he kept the newsletter as a side gig, moved it to Substack on Andrew Chen’s advice, and sent an issue every week for ten months without charging a cent.
Each issue was a long, researched answer to a question product managers and founders kept asking him, like how a marketplace finds its first users or how a PM gets promoted.
The first thousand subscribers came from two guest posts, one on Chen’s blog and one on First Round Review, written by a man with about 5,000 Twitter followers.
Ten months in, something had shifted.
He enjoyed the work, the ideas kept coming, and as he put it, “I finally had the confidence I could do this.”
Then COVID hit, Airbnb looked like it might not survive, and the savings he’d been living on suddenly felt paper thin.
So on April 7, 2020, he turned on a paid tier inside Substack at $15 a month.
“That was more than Netflix,” he said. “How was I going to convince anyone to pay $15 a month?”
But on the first day, 39 people signed up, and another 450 within six weeks.
Paying readers also got into a private Slack group, which he seeded himself, picking the first members and making every one of them upload a photo.
By the end of the year he had 3,300 paying subscribers (~$360,000 a year), and an offer from Miro to run product, with Elena Verna promising he’d make millions doing it.
He turned it down to continue writing the newsletter.
“I’ve never been clearer on what I should be doing,” he wrote that year.
What he didn’t have yet was the thing that would end up earning more than the newsletter itself, and the push to build it came from a podcaster in London who told him, in so many words, that he was an idiot.
The Podcast He Didn’t Want And a Free Year of Software
The podcaster was Harry Stebbings, who in March 2022 had just recorded Lenny for 20VC and told him, “Lenny, you need to do a podcast.”
Lenny translated it for himself as “you should be doing a podcast, idiot.”
He didn’t want one.
Putting his face on camera scared him, which by his own logic meant he had to do it.
He pre-recorded ten episodes with big-name guests before launch, and lined up a revenue stream he had been turning down until then.
For two years, companies had been asking to buy ads in the newsletter, and he’d kept saying no.
Now he wrote back to every one of them and offered podcast sponsorship instead.
Lenny’s Podcast launched in June 2022 with sponsors already signed and passed two million downloads in six months.
Once video was added, YouTube became the only channel that would bring him new subscribers outside of the newsletter, and by 2025 the podcast was out-earning it.
The newsletter itself grows mostly through Substack’s recommendation feature, where more than 5,000 other newsletters point readers to his.
Free subscribers don’t get much.
Of his last ten posts, only two went out free, and on the paid ones a free reader sees the opening section before the paywall drops.
The monthly plan, around $20, gets access to the archive and the Slack group.
The annual plan, about $200 a year, adds Product Pass: a free year of software his readers already use, Cursor, Notion, Granola, Linear, Perplexity and twenty-odd more, worth over $30,000 by his count.
The software companies give the year away and get new users in exchange, and Lenny charges them nothing to be included.
The only money in the deal is the reader’s $200, and all of it goes to Lenny.
So a monthly reader pays $240 a year and gets no tools, while an annual reader pays $200 and gets all of them.
Insider is the next tier up at $400, and gets first access to every new tool and a few that only Insiders get, and companies can buy team seats in bulk.
The pricing page tells readers that “a lot of readers expense Lenny’s Newsletter through their learning and development budget,” and links to an email they can copy to their manager.
The bundle let him lift the annual price from $150 to $200, and in his words it “didn’t accelerate my free subscriber growth, but it did do a lot of good for my paid subscriber growth.”
Above the subscription, the ladder keeps climbing, and at every rung someone else is paying for the right to stand in front of his readers.
A one-day summit in San Francisco, paid for by Stripe as headline sponsor, takes applications from senior product leaders and sold out this year off nearly 3,000 of them, with his podcast guests on stage and every talk put online for free afterwards.
A $2,500 Maven course on building with AI is taught by Colin Matthews, his head of education, with up to $1,000 off for annual subscribers.
Two more shows, “How I AI” and “The Skip”, run under his banner with other hosts, and Pen Name, the studio that produces his podcast, sells the ads.
About ten contractors hold all of it together.
Why software companies hand out a free year of their product for nothing, and why a reader’s employer is happy to pay the bill, comes down to what makes his list so valuable.
Fifty Edits Per Post And a Fear He’s Open About
Lenny gets paid three times for the same audience.
Readers pay for the newsletter, often on a company card.
Sponsors pay to reach those same readers on the podcast.
And software companies pay in kind, with a free year of a product they’d normally charge thousands for.
All three are buying the same thing: access to a list where roughly half the readers are product managers and more than a quarter are founders – decision makers who decide which software their company should run on.
What each of the three audiences are worth is on record.
The last time a paid count surfaced, in 2023, he had 18,000 paying readers out of 377,000, which outside estimates put at more than $2 million a year (and the free list has tripled since then).
Each podcast episode pulls 100,000 to 200,000 downloads, and 16 different brands bought sponsorship on it in the past year alone.
And when Perplexity joined the bundle, that one launch handed the newsletter its biggest growth day ever.
For a company like Cursor or Notion, a free year in the hands of that reader is a cheaper route to a paid team account than any ad they could buy.
Every, the newsletter business run by Dan Shipper, sells a similar deal at $288 a year, a subscription that comes with a set of AI tools, except Every raised investor money and built those tools itself.
Lenny’s bundle cost him nothing to build, because the companies approached him.
His cost of getting readers is just as lean.
He’s tested paid ads, SEO and referral schemes and says almost none of it moved the needle.
Recommendations from other Substack newsletters bring in 78 percent of his new free readers and 12 percent of his new paying ones, and he reckons he’d be sitting at maybe 500,000 subscribers without them.
The price for that is Substack’s 10 percent cut plus 3 percent to Stripe, which he calls “absurd” but pays anyway because “I’ve seen folks leave Substack to avoid these fees and their growth slows.”
The reason those companies came to him at all is the part he protects the most.
He spends ten to fifteen hours on a post, some run past a hundred, and each one gets around fifty editing passes before it goes out.
Guest posts take months, because “my goal with each post is for it to be the best thing that person has ever written.”
He picks podcast guests on one test, whether they’d help his readers, and is more than willing to turn away Fortune 500 CEOs who fail it.
Underneath all of it sits a fear he’s very aware of: “I’m very afraid of moving into a place of just talking about things that aren’t real and just sound true, but aren’t true at all.”
He calls his own years as a product manager a depreciating asset. He left the job in 2019 so he’s aware he’s not exactly at the coal-face anymore.
Instead, the business is built to never depend on him being the expert.
His podcast guests are still inside companies, building products every day and talking about their real world experiences.
So are the guest writers and the hosts of his two network shows.
But he’s the editor who goes and gets what they’ve learned, polishes it, and puts his name to only what’s real, and editing is the one job in the business that gets more valuable the longer he does it.
CJ Gustafson, from an earlier piece, built Mostly Metrics on the same foundation, readers who control budgets, and sells that access to sponsors alone.
Lenny sells it to sponsors, to the readers themselves, and to the software companies who want in front of them.
Three Things Worth Taking From Lenny
1. Sell your judgment, not your expertise.
If you’re worried you don’t have the most experience, there are other strategies you can pursue.
Lenny hasn’t built a product since 2019 and is upfront about it.
His readers pay anyway.
Every week he talks to people who are still heavily involved in product management, and he decides which of them his readers get to hear from.
That is what readers are paying for: his judgment about who is worth their time.
A practitioner’s knowledge goes out of date, while a good editor’s judgment gets better with every year of practice.
Choosing well is a skill in its own right, and readers will pay for it.
2. Protect the quality of your work, even when it costs you.
Some creators are in it for the money, and readers can tell.
Lenny has walked away from easy money more than once to keep the content clean.
Companies asked to buy ads in his newsletter for two years, and he said no every time, long before he had a podcast to send them to.
Miro offered him millions to come and run product, and he said no to that as well.
He did it because an ad in the newsletter, or a job on the side, would have pulled his attention away from the one thing readers pay him for: the quality of what lands in their inbox.
That is what integrity looks like in a creator business, and it compounds.
Every “no” makes the readers trust him a little more, and that trust is the asset everything else is built on.
The next time money is on the table, ask whether taking it would make the content better or worse for the people who already pay you.
If the answer is worse, it was never free money.
3. Build partnerships where everyone wins.
Lenny’s software bundle is a three-way deal, and all three sides come out ahead.
The subscriber pays $200 a year and gets $30,000 worth of tools.
Lenny gets readers who pay annually, stay longer, and accepted a price rise of a third without complaint.
The software companies give away a free year, and in return they get their product in the hands of the people who decide what their companies buy.
Nobody is counting the cost today. All three are thinking years ahead.
Write down the tools your audience already pays for, and ask the top three to give your paying readers a free year.
Lenny started with a note to himself and a nagging feeling that he had nothing new to say.
Since then he has added a podcast, a summit, a network of shows and a course, and at each step he has stayed inside the work he is good at and handed the rest to experts and companies who wanted to reach his readers.
He also chose a market that pays. Product managers and founders have budgets, and the companies that sell to them have bigger ones.
Seven years on from that first note, the shy engineer who thought everything had already been written now teaches more than a million readers, and he still doesn’t call himself the expert.