From Airbnb to Substack: How Lenny Rachitsky Grew His Newsletter to 475k+ Subscribers

Listen To The Marketing Against The Grain Podcast for The Full Episode
Bailey Maybray
Bailey Maybray


Lenny Rachitsky left his role as Airbnb’s product lead in 2019 and had one thought: How do I avoid getting a real job? He took a stab at consulting and advising. Then he tried the startup world.

Lenny Rachitsky.

In short, it all sucked — until he decided to launch Lenny’s Newsletter, an advice column on all things product, growth, and careers. Though it took time before it grew into his full-time gig, his newsletter now boasts 475k+ subscribers — many of which pay for additional features.

On the Marketing Against the Grain podcast, hosts Kipp Bodnar and Kieran Flanagan asked Rachitsky to dish out his advice for budding content creators and entrepreneurs. To get the full rundown — and to hear a few of Rachitsky’s anecdotes and stories — listen to the episode on the HubSpot Podcast Network.

1. Look at What Gives You Energy — and Do More of It

Rachitsky kept his corporate job at Airbnb for seven years. But the go-go-go nature of the role prompted him to leave. He wanted to take a break, maybe look into starting a company or consulting on the side.

In time, Rachitsky learned the startup world and advising other companies drained him. So, he decided to take his passion for writing and leverage his years of product experience. He launched Lenny’s Newsletter, which invigorated him and kept him energized.

In everything Rachitsky does, he asks himself: Did this suck the life out of him? Or did it give him energy? These two questions help steer his decision making. It convinced him to launch his newsletter and, more recently, start a podcast.

As an entrepreneur, you need to make similar choices. Say no to tasks that drain you and lean more into activities that give you a shot of motivation and excitement. 

2. Test the Waters Before Diving In

When Rachitsky first started his newsletter, he dubbed it “Project Avoid Getting a Real Job.” He asked himself if he could make more money than his previous salary, enabling him to work on his newsletter full time instead of getting another gig.

But it took careful testing before he completely dove in and wrote for his newsletter full time. He first launched his newsletter as a part-time side project, while looking for jobs and working as an investor.

In the beginning, he wrote articles on Medium — some of which went viral, garnering him his first 100 subscribers. He then wrote guest posts on blogs with similar audiences, linking to his newsletter and driving 1k+ subscribers in the process. He then pumped out content for nine months and ended up with 10k+ subscribers.

During the pandemic, Rachitsky decided to take a leap of faith. He offered a paid version of his newsletter and committed to writing full time. His project to avoid getting a “real job” succeeded, after a year of testing and growing his audience.

Entrepreneurship is risky, so try to validate your ideas and build an audience before going full throttle. See if people resonate with your product or content. Try developing a set of customers and measure their willingness to pay.

3. Stay Consistent and Focus on Quality

Rachitsky attributes the growth of his newsletter to producing consistently high-quality content. This means telling compelling stories, incorporating examples, finding data, and conducting research.

He finds that the amount of time he spends on a piece correlates with its success. As Rachitsky puts it, if you keep providing valuable stuff, people will consume it.

Rachitsky’s advice applies for anyone building a brand, whether you create content or sell products. As much as influencers talk about growth hacks, it often comes down to staying focused and paying attention to quality. Before launching anything, ask yourself: How can I improve what I’m creating?

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