How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky

People have been asking me to sit on the other side of the mic for a long time. With my wife’s debut children’s book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I’ve had on this podcast. Michelle asked things no one else would think to ask—and many things I’ve never shared publicly. You’ll 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/1419785184

• The collection of moments that led me to what I do now
• When I added a paywall, and how I knew it was working
• The hidden treadmill behind shipping a newsletter post and podcast episode every week
• The most stressful moments I’ve had in business and in life
• How I think about stress, consistency, and keeping the business small

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Metaview—The AI platform for recruiting

DX—The developer intelligence platform designed by leading researchers

• X: https://x.com/TheRialMichelle

• LinkedIn: https://www.linkedin.com/in/michellerial

• Website: https://www.michellerial.com

• 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-baby

• Am I Overthinking This?: Over-Answering Life’s 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/0763655988

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.