How Lenny Rachitsky made his newsletter more lucrative than a job at Airbnb

Hey friends,

One of our goals at Story Alley is to inspire you, so you can make more bold career moves, build optionality for yourself and reach heights you never thought possible.

And what better way to do so than share the stories of people who have successfully done this?!

Today, we’re bringing you the story of Lenny Rachitsky.

If you work in tech, you’re likely familiar with Lenny and his newsletter. But you may not be aware of the backstory that led to the creation of the behemoth Lenny’s Newsletter has become. With almost 360K subscribers, it’s one of the top Substack publications and earns $500,000 in annual revenue (!!).

This is the story of how this happened.

Lenny started his career as an engineer and spent the first 10 years of his career building software products in Silicon Valley. Then, in 2010, he decided to start a startup.

At the time, Foursquare was a big hit. Everybody was checking in and sharing their location, which got Lenny thinking: what if travelers could use locals’ knowledge of a given city or area?! The result was Localmind, a startup that enabled people to tap into the expertise of locals while traveling. The idea took off quickly, and in less than two years Localmind was acquired by Airbnb.

Lenny spent the next seven years of his career at Airbnb, where he led product growth, introduced data-driven culture into the company and built their first host community platform. As a result, he learned a lot and started writing online to share his knowledge. One of his blog posts went viral on Medium and was featured on the publication’s front page. Then, one of the founders of Airbnb shared it with the rest of the company. The accolades were rolling in but Lenny found himself itching to get back in the startup game. In the spring of 2019, he decided it was time to move on.

Upon leaving Airbnb, he gave himself a deadline: he would spend the next six months angel investing, writing and playing around with startup ideas. The goal was to find an idea he wanted to build after this period was over.

The more he experimented, the more he found himself drawn to writing. He enjoyed the process and it gave him more energy than it took away. Plus, people seemed to really like his takes on product and growth.

So, after a few conversations with friends, Lenny decided to put aside all startup ideas and focus on writing full-time. His track record of writing during his Airbnb days had helped him grow his Twitter presence, so when he announced he was launching a newsletter, he had a ready audience for it.

To speed up growth, he started contributing to the blogs of Andrew Chen and First Round. Needless to say, he always linked back to his newsletter. This allowed him to quickly grow his subscriber base to 1,000+ people.

From there, the flywheel started spinning.

Within the next nine months, Lenny’s Newsletter would grow to over 10,000 subscribers. The main growth channels? Twitter and word of mouth.

The more he focused on creating quality content that would help founders, marketers and product managers become better at their jobs, the more people seemed to like and share his newsletter. So, he doubled down on what worked: sharing advice people found valuable week after week.

By 2021, the unimaginable happened: his newsletter had started generating more revenue than his job at Airbnb, including his stock grant (!!).

This was especially impressive because he never thought that writing would turn out to be the highest paying job he ever had. In fact, Lenny started his newsletter because he wanted to optimize for work he found enjoyable and minimum stress. Little did he know that this would turn into a business with an annual revenue of $500,000 that would grow larger with every new subscriber.

Lenny’s story goes to show that sometimes the best thing you can do is optimize for work you find interesting and fun. If you like what you do and consistently share your ideas, people will notice. And this could be the beginning of a brand new journey that would change your life for the better.

With love,

Team Salley

What is Salley?

​Salley is building an intelligent learning assistant, so you can future-proof your career. Learn high-value skills, such as building a strong online presence.