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How Lenny Rachitsky Makes $500K/Year Living a Happy Chill Life

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In today’s episode, I talk to Lenny Rachitsky, creator of the #1 business newsletter on Substack. Lenny has a REALLY interesting career path. He started off as an engineer, then decided to start his own business, which got acquired by Airbnb, where he stayed and worked for over 7 years until he quit to be his own boss again!

When Lenny left Airbnb to tinker with the different startup ideas, he was writing on the side to share his learnings. But then his writing started to gain a lot of traction online… and it became his MAIN hustle!

On an Indie Hackers post, he said the newsletter is making around $500k in annual recurring revenue, so I had to invite him over to hear about how he runs his one-person business. Go check out his newsletter at It’s pretty awesome.

And if you’ve ever wanted to learn about how to be a content creator or start your own newsletter, then you’ll love this episode.

In this episode, you’ll enjoy 3 BIG things:

  1. How to make just enough income to live a happy chill life
  2. Why starting a newsletter might be easier than starting a podcast
  3. What is Lenny’s #1 source of referral traffic

And if you enjoy listening to the podcast, I would really appreciate it if you left a review on Apple Podcasts to help more people find out about it. I might shout you out in the next episode!

By the way, if you want to launch your own business but don’t know where to start, I reopened my course Monthly1K for just $10. It’s helped thousands of people start their business journey and I know it will help you, too. Head over to and sign up.

Check Out: If you want to start or grow an online business, sign up to get the hottest software deals straight to your inbox.

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One response to “How Lenny Rachitsky Makes $500K/Year Living a Happy Chill Life”

February 17, 2023 at 12:43 pm

Amazing how much money a newsletter can produce.

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