Lenny Rachitsky’s $500K a year newsletter has zero employees

Updated September 2026. Originally published February 2023.

Lenny Rachitsky makes around $500,000 a year from a newsletter, and at the start he thought it was the thing getting in the way of his real business.

He’d left Airbnb in March 2019 after seven years as a senior product manager. He had a spreadsheet of about 50 startup ideas, sorted by what excited him, where he had an unfair advantage, and how big it could get. One was a nice gas station, Whole Foods meets gas station, “gas stations for women” is how they pitched it. Another was a little voice in your ear that walks you through your morning routine with music. He wore a microphone clipped to his shirt for a few weeks recording routines for friends.

In between, he started writing down what he’d learned at Airbnb so he wouldn’t forget it. One post landed on Medium’s homepage. He wrote a few more.

“I felt like this writing was a distraction. Why am I writing? There’s no future to writing. I gotta work on the startup thing. But it kept going well.”

A friend told him the obvious. You’re enjoying this, people value it, and finding a thing people value is rare. Forget the startup for a bit. “He proved to be true.”

It’s the plot of Small Time Crooks, one of my favorite movies. The guys open a cookie store as a front to rob a bank, and the cookie store is what takes off. If your side thing is working and your main thing isn’t, the market already voted. It’s the entire idea behind Million Dollar Weekend: find the thing people already pay for and do more of that.

Nine months before charging a dollar

He moved from Medium to Substack because it collected email addresses, with no plan to charge. Then he wrote every week for nine months to find out if he could stick with it and enjoy it. Only after that did he turn on paid.

“I think I got to $10,000 probably in the first couple of weeks, in ARR dollars.” His honest version is the first couple of months after launching paid, about a year after he started writing. He won’t give exact revenue, but “I make a lot more doing this than I made at Airbnb. Significantly more. It’s an absurd amount compared to what I used to do.”

The advice he gives people trying to copy him is the part they skip. “You need to provide value to people. Write a newsletter that is actually valuable to someone. That’s the seed you have to get right.” If people aren’t sharing it, you haven’t earned the growth tactics yet. And the sharing happens somewhere I didn’t expect. “LinkedIn drives more new subscribers to my newsletter than Twitter.” He spends more time on Twitter and it’s more fun, but people on LinkedIn are professionals looking for help. If you’re at zero, I wrote up how to get your first 100 subscribers.

Seven contractors, zero employees

The business was designed around one sentence.

“The writing started off with, I just want to live a really chill life. I’m not gonna work that hard, and I’m gonna try to make just enough income to live a happy, chill life after my intense time at Airbnb. So my whole philosophy was keep it simple. Don’t shoot for the stars.”

So the team is seven contractors and no employees, and he’s avoiding employees as long as he can. Hiring means paperwork, 401ks, taxes. It also means “taking on someone’s livelihood,” career paths, performance reviews. He managed for years and says it’s not the funnest thing.

The org chart fits in one paragraph. Contractors email their hours to his EA, Lindsay, who pays them through Gusto. A guy named Shray leads a Slack community of about 10,000 paying subscribers and oversees the people running meetups and the mentorship program, so Lenny mostly talks to Shray. The copy editor gets drafts by email. The designer gets requests by email. Most of the contractors have full time jobs and like it as a well paid side gig. Lenny still does the core work, the writing and the podcasting, himself.

The podcast, by the way, is on track to make more from ads in its first year than the newsletter does, which he did not expect. My show gets about 10,000 downloads an episode and the sponsor money was fine, nothing exciting. The difference is who’s listening.

“The listeners work at mostly B2B SaaS companies and large enterprises. So the LTVs are really high if you can sell them great software. It’s worth spending to get a big company.”

His sponsors are Amplitude, Miro, Sprig, Notion, Coda. The who’s who of software that is not on AppSumo. He also ran a course, two cohorts, about 500 people. “It was very lucrative, very fulfilling, but it was not where my energy was pulling me. Did not bring me joy.” He shut it down and sends people to other people’s courses now. Keep it simple applies to revenue too.

No meetings before 3pm

This is the part I’m stealing. “I have no meetings until three o’clock. I find that I need these huge blocks of time to be creative and think and research.” Mornings are writing and prep, plus trying to avoid Twitter and mostly failing. After three it’s founder calls and everything else. He works one weekend day to stay ahead.

He wanted me to be clear that this is a full time job, for anyone picturing the chill life as no work.

“When you look at a successful podcast, they make it look really easy. It’s just two dudes talking, like My First Million. But there’s so much work behind the scenes. Any content is a huge meritocracy. If people don’t find value in it, they’ll just leave very quickly. They immediately unsubscribe.”

I asked twice whether he could have built this while still at Airbnb. Both times, no. “I was working insane hours and came home not wanting to do any more work. It’s really hard. I tried.” His advice if you do have a job is to be real that it’s hard, then find slices of time and go deep on one thing. His example is Sriram Krishnan, who published maybe three long interviews in a year and that platform is part of how he ended up a partner at Andreessen Horowitz. “Spend three months on something that’s awesome, put it out, then do the next thing.” That matches my thinking on when to quit your job: the plan has to survive how tired you are after work.

The revenue to stress ratio

When we recorded this AppSumo was around 70 people. I love the team and I love not doing all the work. I also get jealous of a guy with seven freelancers and none of the overhead. So I asked what it’s really like.

“It’s amazing. The revenue to stress ratio is divided by zero. Basically it’s a no-stress life. I get pings every day from people about how much the stuff I put out has helped them. And people are basically paying me to learn and share what I’ve learned.”

His caveat is that he only enjoys this because he already did 15 or 20 years of intense work without a break. “This is my fourth career.” When he hit 200,000 and then 300,000 subscribers, he and his wife went out for a nice dinner. Then: “300,000, sweet. That felt really good. All right, 300,001. Here we go.” Mostly he goes back and works harder.

His last line was for anyone about to write issue one. “Am I actually excited about this, or am I just doing it because everyone’s paying attention to this topic? Make sure you actually care, because it’ll show.”

The distraction was the business. Write the next one.

From episode 286 of my podcast, Noah Kagan Presents. Listen on Spotify or Apple Podcasts.