Loneliness, missing office culture, and team size

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.

We discuss:

1. The collection of moments that led me to what I do now

2. When I added a paywall, and how I knew it was working

3. The hidden treadmill behind shipping a newsletter post and podcast episode every week

4. The most stressful moments I’ve had in business and in life

5. How I think about stress, consistency, and keeping the business small

—

Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184

—

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny

Metaview—The AI platform for recruiting: https://metaview.ai/lenny

DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Michelle Rial:

• X: https://x.com/TheRialMichelle

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

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

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction and role reversal

(04:06) What would Lenny be doing without the newsletter?

(07:20) The moments that led to starting the newsletter

(09:58) Does Lenny still enjoy the work?

(12:42) Stress management and misophonia

(14:00) The psychedelic trip that changed everything

(15:45) Online happiness course and baseline optimization

(17:30) Thunder round: Lenny’s misophonia worst sounds

(20:20) What makes Michelle’s charts so shareable

(23:55) Where chart ideas come from (and why meditation helps)

(26:59) Where does “Lenny” come from?

(28:54) Being recognized in public

(31:24) Early projects

(36:30) Michelle and Lenny’s yin and yang

(37:49) Missing office culture (but not really)

(39:37) Lenny’s face blindness

(40:47) The $100M fraud attack story

(42:50) Michelle’s childbirth emergency

(47:22) Michelle’s creative process

(51:58) Lenny’s favorite children’s books

(54:00) Product management lessons in parenting

(55:31) Defining product management in five words

(58:23) Why Michelle pivoted to children’s books

(01:01:30) The power of iteration and real experience

—

Resources and episode mentions: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.