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Original: Lenny Rachitsky · 12/03/2026

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Summary

Lenny Rachitsky shares insights on building a successful newsletter and podcast, discussing personal experiences and lessons learned along the way.

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Key Insights

“You’ll hear about the specific moments that pushed me to start the newsletter.” — Discussing the motivations behind starting his newsletter.
“How I think about stress, consistency, and keeping the business small.” — Reflecting on his approach to managing stress and business operations.
“This was so fun, and so special, and I hope you like it.” — Expressing his enjoyment of the podcast conversation.

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Topics

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Full Article

People have been asking me to sit on the other side of the mic for a long time. With my wifes debut childrens book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations Ive had on this podcast. Michelle asked things no one else would think to askand many things Ive never shared publicly. Youll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what most stresses me out, and the scariest moment of my life. This was so fun, and so special, and I hope you like it.Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184Listen on YouTube, Spotify, and Apple PodcastsWe discuss:The collection of moments that led me to what I do nowWhen I added a paywall, and how I knew it was workingThe hidden treadmill behind shipping a newsletter post and podcast episode every weekThe most stressful moments Ive had in business and in lifeHow I think about stress, consistency, and keeping the business smallBrought to you by:WorkOSModern identity platform for B2B SaaS, free up to 1 million MAUsMetaviewThe AI platform for recruitingDXThe developer intelligence platform designed by leading researchersWhere to find Michelle Rial: X: https://x.com/TheRialMichelle LinkedIn: https://www.linkedin.com/in/michellerial Website: https://www.michellerial.comReferenced: What Seven Years at Airbnb Taught Me About Building a Business: https://www.lennysnewsletter.com/p/what-seven-years-at-airbnb-taught How to Make a Living as an Artist: https://essays.fnnch.com/make-a-living Indiana Jones: https://en.wikipedia.org/wiki/Indiana_Jones Joshua Tree National Park: https://en.wikipedia.org/wiki/Joshua_Tree_National_Park Authentic Happiness: https://www.authentichappiness.sas.upenn.edu Misophonia: https://my.clevelandclinic.org/health/diseases/24460-misophonia Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens The Devil Wears Prada: https://en.wikipedia.org/wiki/The_Devil_Wears_Prada_(film) Emily Charlton: https://devil-wears-prada.fandom.com/wiki/Emily_Charlton When Harry Met Sally: https://en.wikipedia.org/wiki/When_Harry_Met_Sally xkcd: Ballmer Peak: https://xkcd.com/323 How Long Can I Call My Baby a Baby?: https://cupofjo.com/2026/02/27/how-long-can-i-call-my-baby-a-babyRecommended books: Am I Overthinking This?: Over-Answering Lifes Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861 Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184 Maybe This Will Help: How to Feel Better when Things Stay the Same: https://www.amazon.com/Maybe-This-Will-Help-Better/dp/1797211250 Jon Klassen books: https://www.amazon.com/stores/author/B00MXOB18Q?ccs_id=9e2a2952-ae68-4b1b-ae95-8ed471bd8e75 I Want My Hat Back: https://www.amazon.com/I-Want-My-Hat-Back/dp/0763655988Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: Read more

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Originally published at https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter.