Lenny Rachitsky merely thought he’d share some tips. The career software engineer and executive decided to write about seven things Airbnb taught him about building a business. He’d spent seven years at the company, leaving in 2019 as the leader of the team overseeing wooing consumers to the travel platform. Maybe someone would think his tips were valuable.
Advice columns have been a staple in American life since Marie Manning, writing under the pen name Beatrice Fairfax, began penning “Advice to the Lovelorn” at the New York Evening Journal in 1898. Since the dawn of the internet age, this durable staple has found new life with the advent of the blog (and, more recently, TikTok), where thousands of would-be Beatrices now dispense counsel on everything from personal finance to fashion to where to get your poodle groomed. They hope their advice is appreciated. But most of all, they hope their advice generates revenue—in the form of clicks, shares, and perhaps paying subscribers.
It is, shall we say, a crowded market: There are more than 600 million blogs currently on the internet. Which makes Rachitsky’s story all the more incredible.
Today his weekly newsletter, simply titled Lenny’s Newsletter—“A weekly advice column about building product, driving growth, and accelerating your career”—is one of the top five on the Substack platform. According to his signup page, he is approaching a boggling 500,000 subscribers. He also hosts a top 20 tech podcast (Lenny’s Podcast), manages a popular job board (you’ll never guess what it’s called), and maintains a buzzy community on Slack.
All of which begs the question: What does Rachitsky, an everyday, nice-guy former middle manager in corporate America, have that a few hundred million other bloggers still struggling to find an audience don’t?
“There is a ton of content out there, but not a ton of great content,” Rachitsky says when we speak. “The way I approach this stuff is there’s this ‘jobs to be done’ framework. You’re basically doing a job for someone, solving a problem for them. Most newsletters are not doing that well.”
A happy accident
Lenny’s Newsletter started, as these things often do, by accident. Rachitsky, 41, had moved to the U.S. with his family from Ukraine at age 6, bouncing between California and Canada. A software engineer, he eventually founded a company that he sold to Airbnb, which hired him on. But burned out after his long tenure, he left.
Before he could even figure out what he might do next, he found himself answering email queries from founders asking for advice. Rachitsky decided he’d float a newsletter and see if anyone bit. His first issue was about how to kick-start and scale a business, with counsel from 20 founders and early employees.
People liked it—a lot. “I found that maybe I had things I could share that people would find useful,” he says. “And I just kept down that road.”
Rachitsky emphasizes that he’s just putting his thoughts out for the world to either accept or reject (“I definitely don’t consider myself a journalist,” he says), but he’s being humble. In both his newsletter and podcast, he often interviews experts, as he himself comes off as the approachable, genial coworker just trying to help you figure out your shit.
“It’s both specific enough to be immediately put into action, and also universal enough to matter to anyone thinking about their careers or hiring or pricing or generally how to do better in their professional lives. It’s guidance or knowledge that’s simple and direct,” says Substack cofounder Hamish McKenzie, whose platform boasts such high-profile business bloggers as Joe Pompliano and Matt Stoller. “He has enough material to fill an entire MBA program.”
Rachitsky won’t disclose how many of his almost half a million readers pony up the $150-a-year subscription to get access every week. (Non-payers get acccess to just one issue a month.) While he’s clearly not pulling in $75 million a year (“Very, very safe to say,” he relays with a laugh), even if only a fraction of that readership is paying, he’s still making serious bank. “I had zero belief this was going to work,” he says. “My wife, she’s a writer, and she’s like, ‘What are you doing? You can’t make money writing on the internet.’”
The secret to making money writing online
But it turns out you can. What began as a traditional advice column tackling reader questions each week has evolved into a must-read around entrepreneurship, capital, regulation, and market forces. “There are just so many pieces of building a successful startup,” Rachitsky says. “And I feel my mission is to fill in all of those puzzle pieces so that anyone who’s starting a company has answers to all of these different steps: How do you raise money? How do you hire your first employee? How do you grow a specific product? There are so many of these puzzle pieces that you have to get right.”
There’s still a fair amount of surprise that registers openly on his face when he talks about this stuff, as if he’s constantly pinching himself. Which may be why he’s interested only in maintaining his success, rather than building upon it.
“I am actively trying not to build an empire or create any sort of big thing that I have to manage and run,” he says. “I’m trying to keep it really simple and just let a good thing happen.”
Sounds like sound business advice to us.
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