How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky
In a Nutshell
Lenny Rachitsky built a 1.2M-subscriber newsletter and top-10 tech podcast by following personal "pulls," sharing practitioner wisdom through guest posts, and embracing a high-output treadmill despite stresses like fraud and family health scares. Key to success: Venn diagram of enjoying it, being good at it, and audience love; tools like meditation, psychedelics, and optimism courses manage baseline happiness. Wife Michelle Rial reveals her viral charts process—simplify ideas from lived experiences under optimal conditions (single-shot coffee, deadlines)—and promotes her upcoming children's book *Charts for Babies*, launching April 7th.
These notes were generated by AI and may contain inaccuracies.
Sat on a rock on a substance during a bachelor party trip to Joshua Tree while starting the newsletter. Experienced deep breathing and phrase "I have wisdom to share" repeating for 3 hours with visualization of sitting Buddha. Gave confidence to share wisdom.
What do you want to say to our mothers right now? Do you want to take this back?
Started newsletter in 2019, now has 1.2 million subscribers.
Best stuff comes from actual experience. Source of best advice is from practitioners. Most posts now are guest posts sharing best things learned in careers.
If you hadn't started that newsletter? On the struggle bus of startup life, probably. And then probably after that failed, I would have joined some company as a PM.
Can't imagine doing something more fulfilling and interesting. Visual of Indiana Jones boulder chasing constantly, like a treadmill.
Guest is wife Michelle Rial interviewing Lenny. Shares never-shared-before things, including hardest moments. Day of release is Michelle's birthday; she's publishing third book, children's book Charts for Babies. Pre-order it.
OpenAI, Cursor, Perplexity, Vercel, Plaid, hundreds of winning companies powered by WorkOS. For enterprise software, integrates SSO, SCIM, audit logs. Turns deal blockers into drop-in APIs for B2B SaaS. Stripe for enterprise features. workos.com.
Teams like ElevenLabs, Brex, Rippling, Dealroom, 5,000 organizations use Metaview AI for hiring. AI agents find candidates, take notes, gather insights. Saves hours per hire, closes roles 30% faster. Try free at metav.ai/lenny.
Michelle interviews Lenny because people ask why he doesn't get interviewed. Fun opportunity tied to her book. Lenny will ask about her book.
Newsletter started 2019, 1.2 million subscribers. Podcast frequently top 10 tech podcast.
When met, Lenny was software engineer, then product engineer, product manager at Airbnb for 7 years.
If hadn't started newsletter: Plan A start company, Plan B join startup as first PM, Plan C big company PM, Plan D advise/consult. No plan for current path.
Tinkered with startup ideas, prototyping. Wrote on side what learned/wanted to share. Michelle said can't make money writing on internet, focus on startups/tech.
Why are you writing? You can't make money on the internet writing.
Followed pull. Probably would have started company, failed (most do), then joined as PM, on struggle bus.
Collection of moments following pull.
- First Medium post "What I Learned at Airbnb" did well, featured by Medium, shared company-wide by Brian Chesky.
- Wrote more on Medium, people liked it.
- Conversation with friend Lee Jacobs (now VC): Enjoying it, people like it (rare Venn diagram), pursue and double down, maybe monetize later.
- Nine months weekly Substack newsletter. Lindy effect: as long as survived, likely same in future. Decided could do another 9 months, added paywall.
- Airbnb stock assumed valuable, but COVID hit. Needed to monetize: launched paywall, worked, meaningful dollars first month.
Venn diagram: good at it, people like it, enjoy it.
Yes, most fulfilling/interesting: write about interesting things, share insights/experiences, interview, extract wisdom. Own thing.
Artist Finch blog "How to Become an Artist": don't become professional artist, obligation changes it.
Downside: must produce weekly post + podcast = treadmill, Indiana Jones boulder. Love it some weeks, want break others. Necessary for consistency/survival.
Long-term question: someday can't do weekly (age 60/70/100?). No answer for lifelong Substack/podcast path. Lindy: 2019 start = 7 more years.
Doesn't seem stressed except potty training/sleep. Less stressed than average: 70% genetics ("it'll be all right"), learned to adjust thinking, not take seriously.
Tools: 10-day silent meditation before key post; Joshua Tree psychedelic experience; UPenn online psychology of happiness course (transformative).
Happiness course: science to increase baseline happiness (not peaks/troughs). Optimism/positive thinking key (not gratitude as much). Everyone has baseline; amazing/terrible events return to it. Improve baseline.
Exercise: doesn't make happier, lifts from negative to zero (prevents depression). Used to run.
Bachelor party trip Joshua Tree, psychedelics. Sat on rock 3 hours as newsletter starting: deep breathing, "I have wisdom to share" repeating, Buddha visualization. Gave confidence to share.
What do you want to say to our mothers right now? ... My mom. Okay, Mom. I did some stuff.
Misophonia: brain disorder, bothered by certain sounds, especially eating.
Sound rankings (10 worst):
- Chewing mouth open: 10
- Nails on chalkboard: 5-6
- Newborn baby crying loud: 8
- Gas blower loud nearby: 7-10
- Jude saying "papa" or laughing: 1 (best)
Awkward to ask people to stop eating.
Books: Am I Overthinking This? (many copies sold), Charts for Babies (third book, upcoming).
Charts viral: shared on socials, stolen without attribution, sold on swag (pillows/mugs). Bothered her, stopped looking.
Why sharable:
- Detached from creator.
- Makes her laugh/cackle/tear up (seen in own brain, still funny/emotional).
- Simple, quick, shows something new.
- Short attention spans.
- Makes feel something.
- Low physical labor (brain overthinks, but simple wins).
Sometimes viral via photo of book page, not high-quality digital.
The newsletter feels interesting and good without waiting for external approval or feedback. Working on charts involves thinking many levels deep, sometimes making them too clever. People have short attention spans, so simplify by pulling back layers to make them accessible.
You're my editor sometimes.
I try but you're like no, I don't care about your feedback.
You're usually probably right.
Ideas come from living life, noticing and observing things. Meditation helps by teaching to observe thinking, like noticing anxiety about random things in new ways. Focusing too much on work stops living life and generating ideas. Children's books involve children's concepts, while adult content requires living and noticing. David Sedaris says yes to everything for experiences to fuel stories, like going to Vegas spontaneously. Live real life, try stuff, do crazy things to generate ideas.
Children's book came from observing parenthood and early new parenthood moments. Started charts for new parents in a notebook, but after reading kids' books, rhythm of children's book rhymes emerged. Turned to the back of the notebook to write rhymes. Started front with parent charts, filled some, then in the park decided to write children's book for kids or babies, filling from the back.
I love that. This is another example of just following pull and not just doing the thing that you're doing. Just like, huh, this is pulling me and I'm going to try it and just see where it goes.
Full name is Lenny, not Leonard. Moved to US from Ukraine (Odessa). Official name was Leonid, but called Lenny. Changed to Lenny upon citizenship. Leonid is Russian name or star constellation. Parents asked friends for English version of Luna, got Leonid.
Michelle's family nickname is Lick or Grunchic, Russian little nickname. Strangers cannot call her that.
In Bay Area, people recognize Lenny, started with podcast after 4 years of newsletter (face was tiny Twitter profile before). First time very weird, now happens a lot. Likes it, flattering, people nice, no bad experiences. Please say hi. Asks favorite podcast episode or newsletter, founder or product person story.
Even with headphones at coffee shop or playing with kid, people considerate, 99% very conscious. Not a problem. Doesn't want people to feel they can't talk.
Delightful instance: In Marin, San Anselmo, walking with Michelle, guy in red car with son yells "Lenny, I love your podcast." Held up traffic. Met later, runs hamburger club in Marin.
No early hints pointing to newsletter. Completely unexpected. Never written online before, introvert staying behind scenes. Started during COVID, could type and put out online without going out.
Early side projects through college:
- Atheistpot.com: Reddit for atheist news. Went to atheist conventions. Google AdWords monetized with ironic religious dating site ads like Christian Mingle.
- Tutorials: Tutorials for you by you. People contribute how-tos (how to make eggs, quick shower). Ahead of time, like TikTok, YouTube, before Wikipedia.
- Localmind: Startup sold to Airbnb. App on Foursquare/Gowalla to ask questions of people checked in anywhere (e.g., long line at the mall, what's the special). Cool but nobody needs often, once a quarter. Google now does similar (is it busy?).
DX: Developer intelligence platform for AI era. Answers: which tools working, how used, driving value. Used by Dropbox, Booking.com, Adyen, Intercom for AI value and engineering productivity insights. Visit getdx.com/lenny.
Michelle was Lenny's first online date on HowAboutWe. Had thing for designers. No regrets, good yin-yang: Michelle neat, Lenny chaotic messy process. She's unstressed unbothered, he's bothered with things everywhere. Have cleaners.
No coworkers except Michelle at home. Misses office culture? Always said no, loves solo, but now misses jamming with someone. Has team, Michelle, Twitter, goes to coffee shops (headphones on, focused). Like bowling alone. Misses someone next to working on same thing. Avoids full-time employees to keep simple, prevent creating hated job by chasing opportunities.
Harder now with strangers approaching due to face blindness. Doesn't recognize people who know him, wonders if podcast listener or acquaintance. Bad at remembering names, like texts from new numbers. Michelle sometimes assists like Devil Wears Prada: "That's Emily from Airbnb." Apologizes if doesn't recognize, gotten worse with more podcast/newsletter people.
Business stress: Product pass gives subscribers 23 products (Linear, Mob, Lovable, Replit, Gamma). Used to read all, now too many. Launch year ago: free year of Cursor, Lovable, Bolt, Replit, V0 (5 products). Too good, attracted fraudsters (mostly China rings). Exploits in API, worked with Stripe/Substack. Engineer Estee didn't sleep for week plugging holes. Woke up every night, hard to sleep, viral in China student networks. Risked trust in Lenny.
Personal stress: Baby birth complicated C-section. Induction failed. Epidural went wrong direction (up instead of down), stopped heart/lungs. Intubated, emergency, baby out. Hour to recover, nearly ICU. Lenny waited in hall in bunny suit scrubs, heard beep, doctor ran out/in, others rushed. 10 minutes pacing, no info. Told to repeat "it's gonna be okay," trust hospital/doctors. Anesthesiologist: 1 in 50,000 chance, worst scenario, very rare/dangerous. Lenny held baby hour alone. Baby prefers papa now, plus dog.
They discuss a childbirth story where the partner handled it well under pressure. The speaker recalls being numbed in lungs, unable to breathe, then numbed spinal brain stem and passing out under general anesthesia. It was the scariest moment of life, with no memory of the event. Later read the report months after, had cousin Lois, a nurse, review it; she was shocked. Used tools to stay calm, avoiding spiral. Had a doula who left for the C-section as she couldn't be there.
Charts pop out suddenly with little iteration. Process: perfect amount of coffee, single shot latte at least an hour before. Concept of bomber peak from XKCD: optimal alcohol for insight/creativity. Similar personal coffee chart: genius zone then panic attack. Coffee as drug; too much leads to erratic tangential ideas like spider on caffeine (erratic web vs. LSD web). Single shot optimal; sometimes time limit (2 hours) makes feel like a machine. Writing ideas out in world, visualizing on paper. Not strong at drawing. Influenced by childhood math with dad: fractals, visualization, patterns, mathematical thinking. Visualize ideas simplest way possible.
- Single shot coffee for neuro stimulation
- Deadline, e.g., 2 hours before somewhere (not 30 minutes)
- Good night of sleep (bad sleep + too much caffeine = frantic, no ideas)
- Experiences, thinking, overthinking them
Favorite: John Klassen books, beautiful and sweet (actually involve death, e.g., bear ate bunny, stole my hat). Dr. Seuss too long (50-60 pages), made-up animals like Zong, Vipper from VIP; rhythm nice but teaches unreal things. Anything in Spanish. No strong overlap of kid's favorite that became parent's.
Product management about influence, like parenting. Authority with responsibility. Makes bedtime chart: 3 books, star system. Reads books on parenting (shorten bedtime, sleep through night); relies on what smartest people figured out, not intuition.
In five words: impact, collaboration, judgment, alignment, coordination. Crazy weird job with organizing, planning, outcomes. PM as mini CEO: think like CEO for specific product/feature to grow business, deliver impact by prioritizing/solving impactful problems.
Product management helps current role (editor-in-chief, copy editor, editor, designer): organization, high quality bar, succinct communication.
Wanted children's book from first adult book; charts teach opposites, colors, shapes, feelings, big/small, up/down, overlapping colors. Second book on feelings next year. Idea abstract until trying adult book; rhymes/cadence came quickly. Dad geophysicist pushed math young (girls not encouraged); showed patterns, flips. Did same with son. Experience with son as baby helped; learned teaching, speaking to kids. Pre-kid children's book attempt not good; now natural.
Best stuff from actual experience: pre-kid book weak, post-experience great. Read many children's books to enter zone.
Key: posts from practitioners doing the thing, not pontificators. Guest posts: best thing learned in career.
Iterations: Charts at least 5 (median), maybe 100. Newsletter posts ~50-60 passes + editors/designer. Set aside unfinished work, return with improvements or new ideas; risk others beating to it.
Releasing April 7th, all retailers, local bookstores. Age 2-4 (baby 0-infinity, still call almost-3-year-old baby). End papers: sizes, shapes, lines, numbers, directions, feelings, colors, amounts, sharing, concepts, relationships, opposites. Early learning, funny, simply illustrated rhyming. Lots of iterations, editing; spend more time (old boss Vlad).
Find Michelle: michelérial.com, Instagram. Pre-order/buy Charts for Babies.
Keep Lenny's Podcast in your library
Save the videos and channels worth coming back to, and find them again in one place.
