Lenny Rachitsky12 March 2026

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

8Frameworks

14Insights

Episode overview

Michelle Rial turns the tables on her husband, Lenny Rachitsky, to examine how experiments on Medium and Substack grew into a 1.2-million-subscriber newsletter and a top-10 tech podcast. Lenny traces the role of practitioner-led writing, repeated iteration, and following promising creative pull, while candidly discussing the weekly publishing treadmill, fraud against his subscriber product bundle, and a frightening family medical emergency. The pair also compare their creative processes and discuss Rial's forthcoming children's book, Charts for Babies.

Key ideas

Lenny's publishing career emerged through a series of reinforcing experiments rather than a predetermined plan: an Airbnb essay performed well, Lee Jacobs encouraged him, and nine months of weekly publishing proved sustainable.
The strongest professional advice comes from practitioners sharing lessons earned through direct experience, which is why many newsletter editions are guest posts.
Creative work benefits from following genuine pull: both Lenny's newsletter and Michelle's children's book began as side directions that felt unusually compelling.
Consistency creates a treadmill: every newsletter post and podcast episode is immediately followed by the pressure to produce the next one.
Quality comes from extensive iteration and editing; Lenny estimates revisiting a newsletter roughly 50 times before editors and a designer contribute.
Michelle's best chart ideas come from observing ordinary life, having varied experiences, meditating, and reducing an insight to a simple visual that evokes emotion.
Lenny manages stress partly by deliberately cultivating optimism and raising his baseline happiness, lessons reinforced by a University of Pennsylvania course.
Keeping the business deliberately simple helps Lenny avoid turning an independent creative career into a complicated job he dislikes.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Peak Performance4 steps

Engineering the Creative Peak

Single-shot coffee, a two-hour deadline, and a good night's sleep — dial in the state, not just the effort.

Read →

Entrepreneurship3 steps

Follow the Pull

Bet your career on the thing you enjoy, are good at, and others value — even if it's not the plan.

Read →

Strategy3 steps

Practitioner-Sourced Wisdom

The best advice comes from people on the ground doing the thing — not from pontificators.

Read →

Self-Mastery3 steps

Raise Your Happiness Baseline

Big events only move you temporarily — the real lever is lifting the baseline you always return to.

Read →

Marketing4 steps

Simple, Novel, Emotional: The Shareability Formula

Make it simple, make it show something new, make it feel something — then cut the cleverness.

Read →

Communication3 steps

The Internal-Signal Quality Bar

It's done when it makes YOU laugh or tear up — not when someone else approves it.

Read →

Mindset3 steps

The Lindy Commitment Test

However long you've sustained something is roughly how much longer you can trust it to last.

Read →

Communication4 steps

The Relentless Iteration Loop

Read-through, add, repeat 50-100 times, set aside, return — then hand to editors. That's the secret.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 6

Michelle RialMentionsToday, my guest is my brilliant, incredible wife, Michelle Rial, who turns the table and interviews me.
“Today, my guest is my brilliant, incredible wife, Michelle Rial, who turns the table and interviews me.”
▶ Watch at ~1:00approx.
Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“you started your newsletter 2019. And it now has over a million subscribers.”
▶ Watch at ~4:30approx.
Brian CheskyMentionsBrian chesky at Airbnb there was a whole article where we unpacked this moment in their product development cycle
“Brian Chesky shared with the whole company. So proud of what I shared.”
▶ Watch at ~7:30approx.
Lee JacobsMentionsThen I had a conversation with this with a friend, Lee Jacobs, who's a VC now.
“Then I had a conversation with this with a friend, Lee Jacobs, who's a VC now.”
▶ Watch at ~8:00approx.
FinchCoinedthis artist Finch wrote this blog post, How to Become an Artist.
“this artist Finch wrote this blog post, How to Become an Artist.”
▶ Watch at ~10:30approx.
Jon KlassenRecommendsI love Jon Klassen books. They're so like beautiful and just like sweet.
“I love Jon Klassen books. They're so like beautiful and just like sweet.”
▶ Watch at ~52:30approx.

Resources · 53

PlaidMentionscompany · Zach Perret and William Hockey
“What do OpenAI, Cursor, Perplexity, Vercel, Plaid, and hundreds of other winning companies have in common?”
▶ Watch at ~1:30approx.
Charts for BabiesRecommendsbook · Michelle Rial
“Definitely pre-order it.”
▶ Watch at ~1:30approx.
PerplexityMentionssoftware · Perplexity AI
“What do OpenAI, Cursor, Perplexity, Vercel, Plaid, and hundreds of other winning companies have in common?”
▶ Watch at ~1:30approx.
OpenAIMentionscompany
“What do OpenAI, Cursor, Perplexity, Vercel, Plaid, and hundreds of other winning companies have in common?”
▶ Watch at ~1:30approx.
Charts for BabiesCoinedbook · Michelle Rial
“she is also about to publish her third book, a children's book called Charts for Babies”
▶ Watch at ~1:30approx.
VercelMentionscompany · Guillermo Rauch
“What do OpenAI, Cursor, Perplexity, Vercel, Plaid, and hundreds of other winning companies have in common?”
▶ Watch at ~1:30approx.
SlackUsessoftware · Slack Technologies
“just hit up their Slack support, where they have real engineers in there who answer your questions super fast.”
▶ Watch at ~2:30approx.
WorkOSRecommendscompany · WorkOS, Inc.
“Visit workos.com to get started or just hit up their Slack support”
▶ Watch at ~2:30approx.
DeelUsescompany
“teams like Eleven Labs, Brex, Replit, Deel, and 5,000 other organizations use Metaview”
▶ Watch at ~3:00approx.
BrexUsescompany
“teams like Eleven Labs, Brex, Replit, Deel, and 5,000 other organizations use Metaview”
▶ Watch at ~3:00approx.
ElevenLabsUsescompany · ElevenLabs
“teams like Eleven Labs, Brex, Replit, Deel, and 5,000 other organizations use Metaview”
▶ Watch at ~3:00approx.
MetaviewRecommendscompany · Metaview
“Try Metaview today for free and get an extra month of sourcing at metaview.ai/lenny.”
▶ Watch at ~3:30approx.
AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“When I left my job, I was at Airbnb for 7 years.”
▶ Watch at ~6:00approx.
MediumUseswebsite · Medium
“Like Medium featured it. It went all over the place.”
▶ Watch at ~7:30approx.
SubstackUseswebsite · Substack Inc.
“I decided, I'm going to move to Substack. I'm going to write every week.”
▶ Watch at ~8:30approx.
How to Become an ArtistCoinedother · Finch
“this artist Finch wrote this blog post, How to Become an Artist.”
▶ Watch at ~10:30approx.
Indiana JonesMentionsfilm
“the visual I always have is the Indiana Jones boulder is chasing me constantly.”
▶ Watch at ~11:30approx.
Joshua TreeMentionsplace
“So, it was a trip to Joshua Tree with a friend.”
▶ Watch at ~14:00approx.
Am I Overthinking This?Coinedbook · Michelle Rial
“you have this first book here called Am I Overthinking This, which a lot of people identify with.”
▶ Watch at ~20:00approx.
Bay AreaMentionsplace
“when I walk around the Bay Area in particular, people often recognize me”
▶ Watch at ~29:00approx.
San AnselmoMentionsplace
“I was walking over through San Anselmo with you”
▶ Watch at ~30:30approx.
Hamburger ClubMentionsother
“He runs the Hamburger Club in Marin.”
▶ Watch at ~31:00approx.
RedditMentionswebsite · Steve Huffman, Alexis Ohanian, and Aaron Swartz
“I used to run a website called the atheists pot.com, which was Reddit for atheist news.”
▶ Watch at ~33:30approx.
The Atheist SpotCoinedwebsite · Lenny Rachitsky
“I used to run a website called the atheists pot.com, which was Reddit for atheist news.”
▶ Watch at ~33:30approx.
Google AdWordsUsessoftware · Google
“Google AdWords was a way to monetize your site.”
▶ Watch at ~33:30approx.
Christian MingleMentionswebsite
“So, it was like Christian Mingle and then like all these funny dating sites that didn't make sense for the audience.”
▶ Watch at ~34:00approx.
U-torialsCoinedwebsite · Lenny Rachitsky and a friend
“I worked with a friend on this other project called U torials, which was so ahead of its time.”
▶ Watch at ~34:00approx.
TikTokMentionssoftware · ByteDance
“That's like TikTok. Right?”
▶ Watch at ~34:30approx.
WikipediaMentionswebsite · Wikimedia Foundation
“It was before Wikipedia, I think.”
▶ Watch at ~34:30approx.
YouTubeMentionswebsite · Google
“Yeah, it's like YouTube.”
▶ Watch at ~34:30approx.
LocalmindCoinedsoftware · Lenny Rachitsky and co-founders
“And Local Mind, so that was my startup. We sold to Airbnb.”
▶ Watch at ~34:30approx.
FoursquareUsessoftware · Foursquare
“it was an app that sat on top of Foursquare and Gowalla”
▶ Watch at ~35:00approx.
The MillMentionsplace
“Is there a long line at The Mill, which is near here?”
▶ Watch at ~35:00approx.
GowallaUsessoftware · Gowalla
“it was an app that sat on top of Foursquare and Gowalla”
▶ Watch at ~35:00approx.
DXRecommendssoftware · DX
“To learn more, visit DX's website at getdx.com/lenny.”
▶ Watch at ~36:00approx.
DropboxUsescompany · Drew Houston and Arash Ferdowsi
“With DX, companies like Dropbox, Booking.com, Adyen, and Intercom get a deep understanding”
▶ Watch at ~36:00approx.
Booking.comUsescompany
“With DX, companies like Dropbox, Booking.com, Adyen, and Intercom get a deep understanding”
▶ Watch at ~36:00approx.
AdyenUsescompany
“With DX, companies like Dropbox, Booking.com, Adyen, and Intercom get a deep understanding”
▶ Watch at ~36:00approx.
IntercomUsescompany · Intercom
“With DX, companies like Dropbox, Booking.com, Adyen, and Intercom get a deep understanding”
▶ Watch at ~36:00approx.
ReplitMentionssoftware · Replit
“I launched you get a free year of Cursor and Lovable and Bolt and Replit and V0.”
▶ Watch at ~41:00approx.
Lenny's Product PassCoinedwebsite · Lenny Rachitsky
“I have this product pass. So as a subscriber to my newsletter, you get 23 incredible products.”
▶ Watch at ~41:00approx.
LinearMentionssoftware · Linear
“Linear, Mobbin, Lovable, Replit, Gamma.”
▶ Watch at ~41:00approx.
MobbinMentionswebsite · Mobbin
“Linear, Mobbin, Lovable, Replit, Gamma.”
▶ Watch at ~41:00approx.
LovableMentionssoftware · Lovable
“I launched you get a free year of Cursor and Lovable and Bolt and Replit and V0.”
▶ Watch at ~41:00approx.
GammaMentionssoftware · Gamma
“Linear, Mobbin, Lovable, Replit, Gamma.”
▶ Watch at ~41:00approx.
BoltMentionssoftware · StackBlitz
“I launched you get a free year of Cursor and Lovable and Bolt and Replit and V0.”
▶ Watch at ~41:00approx.
v0Mentionssoftware · Vercel
“I launched you get a free year of Cursor and Lovable and Bolt and Replit and V0.”
▶ Watch at ~41:00approx.
CursorMentionssoftware · Anysphere
“I launched you get a free year of Cursor and Lovable and Bolt and Replit and V0.”
▶ Watch at ~41:00approx.
StripeUsescompany · Patrick Collison and John Collison
“I had to work with Stripe and Substack to just like shut them down.”
▶ Watch at ~41:30approx.
When Harry Met Sally...Mentionsfilm · Rob Reiner
“this is also like a When Harry Met Sally”
▶ Watch at ~43:00approx.
Apple PodcastsRecommendssoftware · Apple Inc.
“you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.”
▶ Watch at ~1:06:30approx.
SpotifyRecommendssoftware · Spotify
“you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.”
▶ Watch at ~1:06:30approx.
Lenny's Podcast websiteRecommendswebsite · Lenny Rachitsky
“You can find all past episodes or learn more about the show at lennyspodcast.com.”
▶ Watch at ~1:06:30approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 3

Hot Take10:30

Turning your passion into work: the Indiana Jones boulder

Even while calling his job the most fulfilling thing he can imagine, Lenny is honest about the cost. Referencing artist Finch's essay 'How to Become an Artist,' he explains that once something becomes a thing you have to do, it changes. The weekly obligation to ship a post and a podcast feels like a treadmill, or a boulder constantly chasing him.

Finch's essay argues you should probably not become a professional artist because obligation changes the thing you love
Producing a post and a podcast episode every single week is a relentless treadmill
The feeling oscillates: some weeks he loves it, some weeks he'd rather skip
Consistency is non-negotiable because you can't survive this way otherwise
He has no answer for where the Substack-writer-podcaster life goes long term

“Because once it's a thing you have to do, it changes it.”
Lenny Rachitsky · 11:00

“So, the visual I always have is the Indiana Jones uh boulder is chasing me constantly.”
Lenny Rachitsky · 11:30

#creator-life#burnout#consistency

Hot Take38:30

You can build a job you hate, so keep it simple

Lenny explains a deliberate constraint on his business: he tries hard to never have full-time employees and to keep things simple. His reasoning is that it's dangerously easy to expand a creator business into something complicated you end up hating, by taking on things that seem big or that people want from you.

He actively avoids full-time employees to keep the operation simple
It's easy to build a creator business into a complicated thing you regret
The trap is doing things people want you to do, or that feel big, until you hate the job you built
He is careful about what he commits to and does

“I also am trying very hard to never have full-time employees. I'm trying to keep things really simple because it's so easy to build this…”
Lenny Rachitsky · 39:00

“you can create a job for yourself that you hate by doing things that people want you to do or by following that feel big…”
Lenny Rachitsky · 39:00

#business#solopreneur#simplicity#creator-economy

Hot Take56:30

A PM really is a mini CEO

Asked to define product management, Lenny pushes back on the common line that a PM is not a mini CEO. He argues a PM should think the way the CEO thinks about their specific product or feature, channeling the question of what would make the business more successful. His working definition: deliver business impact by prioritizing and solving the most impactful business problems.

He disagrees with the standard 'you're not a mini CEO' line and thinks a PM actually is one
A PM's job is to think what the CEO would do on that specific product or feature
His definition: deliver business impact by prioritizing and solving the most impactful business problems
The words he associates with PM: impact, collaboration, judgment, alignment, coordination

“Although I actually do think a PM is a mini CEO. Like, I think people keep saying you're not, but I think you are.”
Lenny Rachitsky · 56:30

“I feel like the PM on the team is basically should be thinking the way the CEO thinks.”
Lenny Rachitsky · 57:00

#product-management#leadership#career

Explainer· 3

Explainer15:30

What a UPenn happiness course taught Lenny about your baseline

Lenny took an online University of Pennsylvania course on the science of happiness and found it transformative. The core lesson: everyone has a baseline happiness level, and big highs or lows always return you to it, so the real work is raising the baseline through optimistic thinking. He also relays a striking finding about exercise: it doesn't make you happier, it just pulls you out of the negative.

Everyone has a baseline happiness level; good and bad events fade back to it
You can raise your baseline mainly by thinking more optimistically and not spiraling into catastrophizing
He found the gratitude exercises less useful than the optimism reframing
Exercise doesn't increase happiness; it moves you from negative to neutral (not depressed)
He believes his own baseline has gone up as a result

“the interesting thing there is exercise doesn't make you happier, but it brings you out of the negative. So, you're negative one without exercise, and…”
Lenny Rachitsky · 17:00

“And the main thing you can do is work on improving that baseline so that you come back to a higher place.”
Lenny Rachitsky · 16:30

#happiness#psychology#mental-health#stress

Explainer21:00

Why Michelle Rial's charts go viral: simple, fast, and felt

Michelle Rial explains that her best charts share a formula: they're simple, quick to digest, and show you something you hadn't thought of before. She knows a chart is done when it makes her laugh or tear up even though she made it. She also notes that over-cleverness is a trap, since short attention spans reward the simplest version.

The winning traits are simple, quick, and revealing something new
Her internal signal that a chart works is that it still makes her laugh or cry after she made it
One chart went viral just from someone photographing a page of her book
People respond best when it's really simple and makes them feel something
Being too clever with too many layers requires simplifying down

“what I like to make is things that are really simple and quick and show you something you haven't thought of before.”
Michelle Rial · 22:00

“People like it when it's really simple.”
Michelle Rial · 22:30

#charts#virality#design#simplicity

Explainer47:30

The creative environment: a single-shot latte, a deadline, and the bomber peak

Michelle describes the conditions she needs to make her best charts: exactly the right amount of coffee (a single-shot latte), a good night's sleep, and a looming deadline that makes her feel like a machine. Lenny adds the concept of the 'bomber peak' from XKCD, the sweet spot of a stimulant where you're most creative before it tips into a panic attack or erratic thinking.

Michelle gets a single-shot latte; too much coffee tips her from genius into a panic attack
A time limit or deadline (ideally about two hours) makes her feel like a machine
A good night of sleep is required; bad sleep plus caffeine gives frantic energy but no ideas
The bomber peak, from XKCD, is the point of just enough stimulant for maximum insight before it drops off
She references the LSD-spider-web image as what too much caffeine does to her output

“which is just the right amount of alcohol where you're the most insightful and creative, and then it falls down”
Lenny Rachitsky · 48:00

“So, single shot latte.”
Michelle Rial · 49:00

#creativity#process#coffee#productivity

Story· 4

Story07:00

The chain of small moments that led Lenny to the newsletter

Lenny never planned to become a Substack writer. After leaving Airbnb his plans were to start a company, join a startup, or become a PM. The newsletter grew instead from a series of pulls: his first Airbnb post going viral on Medium, a friend's nudge to double down, and hitting nine consistent months. He cites the Lindy effect as the reasoning that convinced him to keep going and add a paywall.

His actual plans A-D were start a company, join a startup as first PM, join a big company as a PM, or advise/consult; the newsletter was in none of them
The first thing he wrote online, 'what I learned at Airbnb,' got featured by Medium and shared company-wide by Brian Chesky
Friend Lee Jacobs pointed out he enjoyed it and people valued it, and told him to double down
After 9 consistent weekly months he reasoned via the Lindy effect that he could keep going, so he added the paywall
COVID hit and Airbnb stock looked worthless, which pushed him to monetize; the paywall worked within a month

“There's this uh Lindy effect. I don't know if you know this, but there's this concept of a thing something being Lindy, which is uh…”
Lenny Rachitsky · 08:30

#newsletter#career#origin-story#monetization

Story14:00

The Joshua Tree moment that gave Lenny the confidence to write

Sharing something he says he'd never told publicly, Lenny describes a psychedelic experience on a bachelor-party trip to Joshua Tree as he was starting the newsletter. Sitting on a rock for roughly three hours, he had the phrase 'I have wisdom to share' repeat through him alongside a Buddha-like visualization. It gave him the confidence that he actually had things worth sharing.

Happened on a bachelor-party trip to Joshua Tree involving psychedelics, right as he started the newsletter
He sat in one spot for around three hours with deep breathing
The phrase 'I have wisdom to share' repeated over and over with a sitting-Buddha visualization
It didn't make him write the post directly, but gave him the confidence that he had something to offer

“That made me feel like I can do this. Like it gave me the confidence that like, "Okay, maybe I do have things to share."”
Lenny Rachitsky · 15:00

#confidence#psychedelics#origin-story

Story40:30

The free-tools promo that triggered fraud rings in China

Lenny's most stressful business moment came from a too-good product-pass offer giving subscribers a free year of Cursor, Lovable, Bolt, Replit, and V0. It attracted organized fraud rings, mostly in China, that exploited holes in the API his team had built. He and an engineer worked with Stripe and Substack around the clock to shut it down, fearing it could unravel trust in the whole business.

The offer was a free year of Cursor, Lovable, Bolt, Replit, and V0, five tools, which he calls way too good an offer
Fraudsters, mostly organized rings in China, exploited holes in their custom API
It went viral in China's student network as free goodies
His engineer Este barely slept for a week plugging holes
The real fear was reputational: subscribers losing trust in Lenny

“So I just had so many fraudsters, mostly in China, it turned out. Just like all these fraud rings in China trying to find ways…”
Lenny Rachitsky · 41:30

“you get a free year of Cursor and Lovable and Bolt and Replit and V0.”
Lenny Rachitsky · 41:00

#fraud#product-pass#stress#operations

Story42:30

The scariest moment of Lenny's life: a birth that went wrong

Lenny shares the most frightening personal moment of his life, the complicated birth of their son. During the C-section, Michelle's epidural traveled up rather than down her body, affecting her heart and lungs and requiring an emergency intubation. Waiting in the hall in a sterile suit, Lenny heard alarms and doctors rushing in with no information, and used his self-talk tools to keep from spiraling.

Michelle needed a C-section after an induction stalled
Waiting in the hall, Lenny heard rapid beeping and saw doctors running in with no explanation for about 10 minutes
The epidural went the wrong direction, up the body, affecting her heart and lungs and requiring emergency intubation
The anesthesiologist called it a roughly one-in-50,000 event
Lenny relied on repeating 'it's going to be okay' to stay calm; Michelle has no memory of it under general anesthesia

“anesthesiologist said it was a one in 50,000 chance. And it's like the worst scenario that is very rare and very dangerous.”
Lenny Rachitsky · 45:30

“it's probably the scariest moment of my life.”
Lenny Rachitsky · 46:00

#parenthood#health#stress#personal

Takeaway· 4

Takeaway08:00

The rare Venn diagram: you enjoy it, you're good at it, people value it

Lenny recounts the advice from friend Lee Jacobs that crystallized why he should pursue writing: it's rare to find something you enjoy that other people also value. Michelle points out the missing third circle, that he also liked doing it, making it his own version of Ikigai.

Lee Jacobs framed it as a rare overlap of enjoying something and having people value it
The full trigger required three things: good at it, people like it, and enjoying doing it
Michelle connects this to the Ikigai concept
The 'enjoy it' piece is what makes the difference, not just competence plus demand

“you seem to be enjoying it. People seem to be liking it. Which is very rare, that Venn diagram of things.”
Lenny Rachitsky · 08:00

#ikigai#career#motivation

Takeaway24:00

Ideas come from living real life, not sitting and thinking

Both Michelle and Lenny agree that creative ideas come from experiences, not from sitting down trying to generate them. Michelle says her ideas come from living life and noticing, and that over-focusing on work kills the flow of ideas. Lenny invokes David Sedaris, who says yes to everything so he keeps having stories to tell.

Michelle's ideas come from living life and noticing, and meditation sharpened her ability to observe her own thinking
Focusing too hard on work stops the ideas because you stop living life
Lenny cites David Sedaris saying yes to every invitation to keep accumulating stories
You have to try stuff and do crazy things rather than sit and brainstorm

“The ideas come from just living life and noticing noticing a lot of things”
Michelle Rial · 24:00

“You can't just kind of sit there and come up with ideas. You have to try stuff and do crazy things.”
Lenny Rachitsky · 25:30

#creativity#ideas#process

Takeaway1:01:30

The best advice comes from practitioners doing the thing for real

Lenny credits much of his newsletter's success to sourcing content from people actually doing the work, not pontificators. Most of his posts are now guest posts where a practitioner shares the single best thing they've learned in their career. The broader lesson he draws is that great advice comes from doing the thing and then sharing, then refining it relentlessly.

Most of his posts are now guest posts sharing the best thing someone learned in their career
The best advice comes from people on the ground doing the thing, not floating in the clouds pontificating
Michelle's children's book got better only after she had real parenting experience, reinforcing the point
He pairs 'doing the thing' with communicating it simply and refining it

“So, at this point most of my posts are guest posts where somebody's sharing the best thing they've learned in their career.”
Lenny Rachitsky · 1:01:30

“the best stuff comes from doing the thing and then sharing your advice versus just thinking you know what you're doing.”
Lenny Rachitsky · 1:02:00

#writing#advice#guest-posts#newsletter

Takeaway1:02:30

The unglamorous secret: iterating a post 50-plus times

Both Lenny and Michelle attribute their quality to sheer iteration. Michelle revises a chart at least five times, sometimes closer to 100. Lenny says he rewrites a newsletter post around 50 times, reading through and improving it repeatedly, before his editor, copy editor, and designer touch it. The takeaway they land on is that iteration and editing are the secret to success.

Michelle iterates a chart at least five times, and agrees the real number may be closer to 100
Lenny goes through a newsletter post roughly 50 times, reading and adding each pass
Only after his own passes does his editor, copy editor, and designer get involved
They summarize the secret to success as iteration and editing, or 'spend more time on it'

“So, like when I write a newsletter post, I go through it probably, let's say 50 times making it better.”
Lenny Rachitsky · 1:03:00

#writing#iteration#craft#editing

Key ideas

Frameworks in this episode

Engineering the Creative Peak

Follow the Pull

Practitioner-Sourced Wisdom

Raise Your Happiness Baseline

Simple, Novel, Emotional: The Shareability Formula

The Internal-Signal Quality Bar

The Lindy Commitment Test

The Relentless Iteration Loop

People & resources mentioned

People · 6

Resources · 53

Insights & moments

◆Hot Take· 3

Turning your passion into work: the Indiana Jones boulder

You can build a job you hate, so keep it simple

A PM really is a mini CEO

✶Explainer· 3

What a UPenn happiness course taught Lenny about your baseline

Why Michelle Rial's charts go viral: simple, fast, and felt

The creative environment: a single-shot latte, a deadline, and the bomber peak

❝Story· 4

The chain of small moments that led Lenny to the newsletter

The Joshua Tree moment that gave Lenny the confidence to write

The free-tools promo that triggered fraud rings in China

The scariest moment of Lenny's life: a birth that went wrong

▲Takeaway· 4

The rare Venn diagram: you enjoy it, you're good at it, people value it

Ideas come from living real life, not sitting and thinking

The best advice comes from practitioners doing the thing for real

The unglamorous secret: iterating a post 50-plus times

Hot Take· 3

Explainer· 3

Story· 4

Takeaway· 4