Habits of Great Writers, Founders and Investors

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“The repetition itself becomes the important thing; it’s a form of mesmerism. I mesmerize myself to reach a deeper state of mind.”

Haruki Murakami

Look at the daily lives of great writers, founders and investors. You see the same shape every time. A small set of rituals. Each one specific. Each one non-negotiable.

A ritual here is one practice with a cadence.

Most surveys of great operators (Mason Currey’s Daily Rituals is the canon) show only the creation rituals. Creation without the distribution is misleading. Two thousand words a day in a drawer is two thousand words in a drawer. Creation is necessary but not sufficient.

Ernest Hemingway, novelist

Work:

  • Begins at first light
  • Writes standing at a chest-high bookshelf or typewriter
  • Stops only when he knows what comes next
  • Tracks the daily word count on a hand-drawn chart on the wall
  • Pegs 500 words as a good day
  • Spends the afternoon fishing, swimming or drinking
  • Re-reads the manuscript from the start before writing more

Distribution:

  • Charles Scribner’s Sons handled trade
  • Files an Esquire “Letter” essay roughly monthly from 1933 to 1936
  • Sits for staged photo shoots with his boat, his rifle and the marlin
  • Travels to bullfights, safaris and wars as press fodder
  • Sat for the Paris Review’s “Art of Fiction No. 21” interview (1958) that locked in the writer-as-craftsman myth

Steve Jobs, founder of Apple and NeXT

Work:

  • Wears the same outfit every day (black turtleneck, Levi’s 501s, New Balance 991s)
  • Walks long loops with whoever he wants to talk to instead of holding office meetings
  • Sits cross-legged on the floor barefoot during early Apple meetings
  • Eats the same one or two foods for weeks at a stretch
  • Returns to the same Zen monastery near Los Altos for retreats

Distribution:

  • Apple’s products and retail did most of the marketing
  • Rehearses every keynote for weeks before delivery
  • Delivers four to six keynotes a year at Apple events
  • Granted personal interviews sparingly and only to chosen reporters (Walt Mossberg, Steven Levy, Brent Schlender)
  • Sat for the 2005 Stanford commencement address that became the most-watched commencement speech of all time

Warren Buffett, investor and CEO of Berkshire Hathaway

Work:

  • Spends five to six hours a day reading newspapers, filings and books
  • Drinks five Coca-Colas every day
  • Orders McDonald’s breakfast based on whether Berkshire’s stock is up or down
  • Tap-dances to work, in his own words
  • Plays bridge twelve hours a week online
  • Holds his calendar mostly empty by design

Distribution:

  • Writes the Berkshire annual letter every year since 1965 (never missed)
  • Hosts the Berkshire annual meeting in Omaha (six hours of unscripted Q&A, 40,000+ attendees)
  • Appears on CNBC’s Squawk Box for scheduled interviews each spring
  • Lets the documentary Becoming Warren Buffett (HBO, 2017) be filmed at home
  • Sat for the Snowball biography (Alice Schroeder, 2008) over 2,000 hours of interviews

Toni Morrison, novelist

Work:

  • Wakes at 4 AM
  • Watches the first light come in before writing
  • Drinks coffee before any words
  • Writes on yellow legal pads in longhand
  • Reserves the pre-dawn block for fiction while raising two boys and editing at Random House
  • Edits standing at a tall lectern in the afternoon

Distribution:

  • Random House published her (and she was a senior editor there until 1983)
  • Gives public readings on a touring circuit around each book release
  • Holds a permanent residency at Princeton (1989-2006), building literary community and press access
  • Won the Nobel Prize in 1993 (which then re-marketed every prior book)

Hayao Miyazaki, animator and director

Work:

  • Arrives at Studio Ghibli around 11 AM
  • Stays until 9 PM, seven days a week during production
  • Sleeps on a cot in the studio when a deadline closes in
  • Walks the neighborhood at 3 PM for fresh air and ideas
  • Hand-draws every key frame himself
  • Smokes outside the office under a small awning

Distribution:

  • Studio Ghibli’s distribution deals (Disney internationally, Toho in Japan) handled trade
  • Sits for full press tours around every release
  • Subject of the NHK documentary series 10 Years with Hayao Miyazaki and Never-Ending Man
  • Opened the Ghibli Museum (2001) as a permanent marketing artifact

Charles Darwin, naturalist

Work:

  • Walks the Sandwalk three times a day on a quarter-mile loop
  • Counts pebbles on each lap so his mind can wander
  • Holds three writing blocks of about 90 minutes each
  • Lets his wife Emma read aloud to him after lunch at 3 PM
  • Plays backgammon with Emma every evening
  • Writes six or more letters by hand each day

Distribution:

  • John Murray (publisher) printed On the Origin of Species and sold out the first run of 1,250 copies in a day
  • The 6+ letters a day to Hooker, Lyell, Huxley and Wallace were both work and the entire scientific press apparatus of the era
  • Coordinated the Linnean Society reading of his theory alongside Wallace’s paper in July 1858
  • Sends complimentary copies of Origin to 250 named scientists before publication
  • Let T.H. Huxley (“Darwin’s bulldog”) run the public debate

Jeff Bezos, founder of Amazon

Work:

  • Holds no meetings before 10 AM
  • Saves high-IQ decisions for the morning
  • Sleeps eight hours, every night
  • Opens every meeting with thirty minutes of silent reading of a six-page narrative memo
  • Refuses to read PowerPoint slides
  • Treats a handful of decisions a year as “Type 1” and gives them concentrated time

Distribution:

  • Writes the annual shareholder letter every spring (since 1997)
  • Appends the original 1997 letter to every subsequent letter
  • Delivers keynotes at AWS re:Invent each year
  • Sat for a CBS 60 Minutes feature in 1999 that broke Amazon mainstream
  • Bought the Washington Post in 2013 as both investment and permanent press capital

Charlie Munger, vice chairman of Berkshire

Work:

Distribution:

  • Hosts the Daily Journal annual meeting Q&A (separate from Berkshire’s)
  • Delivers one or two major university speeches a year (USC commencement 1986 and 2007, Harvard Law 1995)
  • Let Poor Charlie’s Almanack (2005) compile his speeches as the canonical artifact
  • Sat for podcast interviews with John Collison, Tren Griffin and Acquired in the final years

Haruki Murakami, novelist and ultramarathoner

Work:

  • Wakes at 4 AM
  • Writes for five to six hours straight
  • Stops at ten pages even if a sentence is half-finished
  • Runs 10 km or swims 1,500 m every afternoon
  • Reads or listens to music in the evening
  • Lights out by 9 PM
  • Holds the same schedule for six months at a stretch while drafting a novel

Distribution:

  • Knopf (US) and Shinchosha (Japan) handle trade
  • Sits for almost no interviews and runs no book tour
  • Publishes short stories in Japanese literary magazines on the cycle between novels
  • Wrote What I Talk About When I Talk About Running as a personal-brand artifact about the running itself

David Lynch, filmmaker

Work:

  • Sits for Transcendental Meditation twice a day, twenty minutes each
  • Has held the same meditation practice since 1973
  • Eats the same lunch for years at a stretch
  • Drinks seven Cokes a day during peak production years
  • Sketches in the same notebook he carries everywhere
  • Watches the weather every morning before starting work

Distribution:

  • Studios and festivals handled film releases (Cannes premiered Wild at Heart and Mulholland Drive)
  • Recorded a daily weather report on his own YouTube channel from May 2020 to his death
  • Released music albums, sold paintings and sold David Lynch Coffee as branded objects between films
  • Hosted the Festival of Disruption in LA and Brooklyn as recurring marketing events
  • Wrote Catching the Big Fish (2006) as the personal-brand artifact for the meditation practice

Andy Warhol, artist

Work:

  • Walks Madison Avenue for an hour every morning
  • Records every taxi fare, meal and tip in a hardback ledger
  • Calls Pat Hackett every morning to dictate the previous day’s events for the diary
  • Keeps a tape recorder running through dinners and parties
  • Carries a Polaroid camera to every social event
  • Photographs almost everyone he meets

Distribution:

  • Leo Castelli Gallery (then Iolas) handled sales
  • Hosts open-door parties at the Factory most evenings
  • Founded Interview magazine in 1969 as his own owned media channel
  • Appeared in TV commercials in the 1980s (Diet Coke, TDK, Pioneer, Drexel Burnham)
  • The Polaroid photos themselves doubled as an art-and-press feedback loop

Benjamin Franklin, printer, statesman and inventor

Work:

  • Asks himself “What good shall I do this day?” each morning
  • Takes a one-hour air bath naked by an open window each morning
  • Swims in open water several times a week
  • Tracks thirteen virtues on a printed grid every day
  • Asks himself “What good have I done today?” each evening
  • Writes the next day’s plan the night before

Distribution:

  • Founded The Pennsylvania Gazette as his own newspaper in 1729
  • Wrote Poor Richard’s Almanack annually from 1733 to 1758
  • Self-published most of his pamphlets
  • Built the postal infrastructure (postmaster of Philadelphia, then deputy postmaster general for the colonies) that distributed his own work
  • Wrote the Autobiography as the founding self-help title in American letters

Bill Gates, founder of Microsoft

Work:

  • Takes two “Think Weeks” a year, alone in a forest cabin
  • Reads a stack of papers and books submitted by employees during each Think Week
  • Reads for hours on Sundays
  • Rocks back and forth while concentrating
  • Travels with a tote bag of physical books

Distribution:

  • Publishes a GatesNotes year-end letter every December
  • Publishes a summer reading list every June
  • Publishes a year-end reading list every December
  • Does Reddit AMAs on a regular cadence
  • Delivers TED talks on a regular cadence
  • Filmed Inside Bill’s Brain (Netflix, 2019) as a three-part marketing artifact

Ray Dalio, founder of Bridgewater

Work:

Distribution:

  • Sends “Daily Observations” to Bridgewater LPs daily
  • Wrote Principles (2017) and ran a multi-year marketing campaign around it
  • Filmed Principles for Success (animated YouTube series, 30M+ views)
  • Posts on LinkedIn regularly
  • Sat for TED talks and CNBC scheduled interviews

Joan Didion, essayist and novelist

Work:

  • Spreads the day’s pages on the dining table at the end of each afternoon
  • Pours one drink and reads back what she wrote
  • Sleeps in the same room as the unfinished manuscript in the final week
  • Keeps a notebook in her bag at all times
  • Tests every sentence by reading it aloud
  • Re-types the prior day’s pages before starting new ones

Distribution:

  • Knopf published her
  • Publishes long-form essays in NYRB, Vogue and Saturday Evening Post between books
  • Sat for the documentary The Center Will Not Hold (2017) directed by her nephew Griffin Dunne
  • Granted the Celine ad campaign (2015) that turned her into a fashion icon at age 80

Twyla Tharp, choreographer

Work:

  • Wakes at 5:30 AM
  • Hails a cab to the gym before her body wakes up
  • Says “the cab is the ritual, not the workout”
  • Trains in the gym for two hours
  • Starts each new project by placing a labeled cardboard box on the floor
  • Drops every clipping, sketch, recording and note into that box for the project’s duration

Distribution:

  • Performance venues (American Ballet Theatre, Broadway) handled the work
  • Publishes a book every several years (Push Comes to Shove 1992, The Creative Habit 2003, The Collaborative Habit 2009, Keep It Moving 2019)
  • Each book seeds the next decade of speaking and teaching work

Ludwig van Beethoven, composer

Work:

  • Counts out sixty coffee beans per cup at breakfast
  • Composes from sunrise to midday
  • Eats lunch at the same tavern most days
  • Walks the woods through the afternoon with a notebook and pencil
  • Writes nothing musical after dark
  • Goes to bed by 10 PM

Distribution:

  • Vienna’s noble patrons (Lobkowitz, Rasumovsky, Lichnowsky) underwrote him with annuities
  • Publishers Breitkopf and Härtel and Steiner printed the scores
  • Self-produces a subscription concert (Akademie) every year or two to premiere new work
  • Prints and distributes his own subscriber bills before each concert
  • Negotiates with multiple publishers in parallel to drive up prices

Sara Blakely, founder of Spanx

Work:

  • Drives a “faux commute” in circles before working from home
  • Journals five minutes each morning
  • Keeps an “embarrassment list” of mistakes
  • Adds to that list every week
  • Writes the day’s intention before opening her laptop

Distribution:

  • Sat for The Oprah Winfrey Show in November 2000 that broke Spanx national
  • Spent 18 months seeding press relationships before that single appearance
  • Department-store buyers (Neiman Marcus first) handled retail
  • Tells the “fax machine and $5,000” origin story at every conference she speaks at
  • Posts to Instagram on cadence with hand-on-camera selfie videos that read as personal

Paul Tudor Jones, hedge-fund manager

Work:

  • Visualizes a trade in detail before placing it
  • Checks the 200-day moving average on every chart before reading any news
  • Risks no more than 1% of capital per trade
  • Writes the trade thesis down before opening the position
  • Marks the calendar five years out from anniversaries of past losses

Distribution:

  • Founded the Robin Hood Foundation in 1988 and hosts its annual gala (one of the largest fundraising nights of the year in New York)
  • Sits for an annual Bloomberg or CNBC interview around the gala
  • Allowed Trader (1987 PBS documentary) to be filmed, then bought up copies for years afterward (the suppression itself fed his mystique)

Stephen King, novelist

Work:

  • Writes 2,000 words a day
  • Same desk, same chair, same start time
  • Writes seven days a week including his birthday and Christmas
  • Plays loud rock music while drafting
  • Refuses to leave the chair until the quota is met
  • Reads four to five hours a day on top of writing
  • Walks four miles in the afternoon

Distribution:

  • Scribner / Viking publish him
  • Writes “The Pop of King” column in Entertainment Weekly for eight years (2003-2011)
  • Tours bookstores for every hardcover release
  • Runs a Q&A page and reply system on stephenking.com
  • Wrote On Writing (2000) as a permanent marketing artifact for the catalog

Tobi Lutke, founder of Shopify

Work:

  • Programs every day even as CEO
  • Reads forty-plus minutes every morning before opening Slack
  • Stops work at 5:30 PM and goes home for dinner
  • Skips most meetings as a rule
  • Sleeps eight hours, no exceptions

Distribution:

  • Shopify owns the merchant channel and does most of the marketing for the brand
  • Tweets and replies on X daily
  • Publishes the annual Shopify Investor Day letter
  • Public memos to his org that he then posts externally (the 2023 “We’re not a family” memo went viral by his choice)

Howard Marks, co-founder of Oaktree

Work:

  • Writes a long-form memo to clients several times a year
  • Walks his dog for an hour every day as thinking time
  • Reads every memo aloud to himself before publishing
  • Avoids macro forecasts entirely
  • Re-reads his own old memos every few years

Distribution:

  • Memos go to Oaktree clients first, then public
  • “bubble.com” (January 2000) and “The Most Important Thing” became investing canon
  • Published The Most Important Thing (2011) and Mastering the Market Cycle (2018) as memo aggregations
  • Sits for podcast interviews on cycle around each new memo

Maya Angelou, poet and memoirist

Work:

  • Rents a hotel room by the month at $200 or so
  • Brings yellow pads, a Roget’s Thesaurus, a dictionary, a Bible and a deck of cards
  • Asks staff to strip the art off the walls
  • Arrives at the room at 6:30 AM
  • Writes lying on the bed
  • Leaves by 2 PM
  • Reads the day’s pages aloud over a glass of sherry in the evening

Distribution:

  • Random House published her
  • Performs her poems aloud at every public appearance
  • Read “On the Pulse of Morning” at Bill Clinton’s inauguration in 1993
  • Records audio of her own work as a parallel artifact
  • Toured the lecture circuit at $50,000+ per appearance through the 90s and 2000s

Yvon Chouinard, founder of Patagonia

Work:

  • Closes the office when the surf is up
  • Surfs in the morning when the waves break at Rincon
  • Climbs at least once a week well into his 80s
  • Eats a long sit-down lunch with employees in the company canteen
  • Spends a full month each year on remote rivers fly-fishing

Distribution:

  • Patagonia catalogs are long-form essays and photography, designed to be kept rather than thrown out
  • Published Let My People Go Surfing (2005) and The Responsible Company (2012)
  • Ran the “Don’t Buy This Jacket” full-page New York Times ad on Black Friday 2011
  • Gave Patagonia to a trust in September 2022 in the single largest marketing event in company history
  • The Footprint Chronicles makes supply-chain transparency a recurring content stream

Stan Druckenmiller, investor

Work:

  • Refuses to take a position without conviction
  • Reviews every open position before bed
  • Stays quiet in meetings until he sees the data
  • Concentrates 80% of capital in one idea when conviction shows up
  • Sells positions immediately when the thesis breaks

Distribution:

  • Delivers one Sohn Investment Conference talk per year. That’s the entire ritual.
  • Sits for almost no interviews outside that single venue
  • Lets the track record speak

Anthony Trollope, novelist and postal inspector

Work:

  • Wakes at 5:30 AM
  • Pays a servant to bring coffee at that hour
  • Writes 250 words every fifteen minutes by pocket watch
  • Targets 2,500 words before 8:30 AM
  • Starts the next novel on the same page if one finishes mid-session
  • Heads to the post office for a full day’s work after writing
  • Treats writing as a craft on the same schedule as cobbling

Distribution:

  • Negotiates every publishing contract himself
  • Serializes new novels in Cornhill, Pall Mall and Saint Pauls before book release
  • Tours America in 1861 and Australia in 1871 and 1875 to seed those markets
  • Publishes the Autobiography (1883) as the marketing artifact for his collected works

Brian Chesky, founder of Airbnb

Work:

  • Holds 1:1 meetings with every direct report each week
  • Stays in an Airbnb listing somewhere in the world several weeks a year
  • Sends a company-wide email every Sunday night
  • Walks the floors of Airbnb stays as a customer

Distribution:

  • Airbnb’s marketplace and brand operation do most of the marketing
  • Posts many of his internal letters publicly on X or the Airbnb blog (the 2020 layoffs letter became a case study)
  • Hosts the annual host conference (“Airbnb Open” and successors)
  • Sits for the Masters of Scale podcast and How I Built This on cycle

Work:

  • Keeps an empty calendar by default
  • Takes meetings on walks instead of in offices
  • Reads physics, philosophy and math an hour or more a day
  • Picks one book and reads it ten times before moving on
  • Eats one or two meals a day with long fasts in between

Distribution:

  • Posts on X (since 2009)
  • “How to Get Rich” tweetstorm (May 2018) was a single session that became a book
  • Sat for The Joe Rogan Experience and The Tim Ferriss Show as career-defining appearances
  • Allowed Eric Jorgenson to compile The Almanack of Naval Ravikant (free book, 2020) from the tweets and podcasts
  • Hosts the Naval podcast on irregular cadence

John Cheever, novelist

Work:

  • Puts on his only suit each morning
  • Rides the elevator down to a basement maid’s room with the other working husbands
  • Hangs the suit on a hanger
  • Writes in his boxers all day
  • Puts the suit back on to ride the elevator home

Distribution:

  • The New Yorker published 121 of his stories over 40 years
  • Knopf published the collections
  • Each New Yorker story was a teaser for the eventual collection
  • Sat for the Paris Review’s “Art of Fiction No. 62” (1976) the year of his comeback novel Falconer

Jack Dorsey, founder of Twitter and Block

Work:

  • Walks five miles to work each morning
  • Eats one meal a day, in the evening
  • Fasts all day Saturday with only water
  • Takes an ice bath every morning
  • Sits in a 220-degree sauna three times for fifteen minutes each in the evening
  • Sits for meditation twice a day, twenty minutes each

Distribution:

  • His own product (Twitter / X) was his marketing channel for a decade
  • Posts personal photos of ice baths, fasting and sauna routines as a content stream
  • Sat for the Tim Ferriss podcast and Joe Rogan as career-defining appearances
  • Uses Bluesky and Nostr now as parallel channels

Marc Andreessen, founder and investor

Work:

  • Keeps an “anti-todo list” of tasks he refused
  • Reads four to five books simultaneously, one per slot in the day
  • Sleeps nine hours a night
  • Sits for ten minutes of mindfulness each morning
  • Naps in the afternoon when the schedule allows
  • Lifts weights and walks the trails near his house

Distribution:

  • Built a16z as a media company that invests
  • Operates a podcast network, a magazine (Future), a content team
  • Posts on X constantly
  • Wrote The Techno-Optimist Manifesto (October 2023) as a market-positioning artifact
  • Sat for Lex Fridman, Tim Ferriss, Dwarkesh, Joe Rogan in 2023-24 as a coordinated press cycle

Cal Newport, computer scientist and author

Work:

  • Plans every minute of the workday on paper at the start of the day
  • Stops work at 5:30 PM regardless of state
  • Runs a written shutdown ritual ending with the words “Schedule shutdown, complete”
  • Walks for an hour or more a day as thinking time
  • Reads five books a month minimum
  • Avoids social media entirely

Distribution:

  • Publishes a new book every 2-3 years (Random House / Portfolio)
  • Sends a Sunday newsletter
  • Hosts Deep Questions podcast weekly
  • Writes long-form essays in The New Yorker on cadence
  • Avoids the X / Instagram / TikTok game entirely and lets the books carry the brand

Patrick Collison, founder of Stripe

Work:

  • Maintains a public reading list of every book he finishes
  • Reads 100+ books a year
  • Memorizes long technical papers by re-reading them
  • Walks San Francisco for hours when working a hard problem
  • Replies to email in batches

Distribution:

  • Stripe owns its developer channel and runs Sessions (the annual conference)
  • The public reading list at patrickcollison.com is itself a marketing artifact
  • Founded Stripe Press in 2018 to republish books (Stubborn Attachments, The Dream Machine, Working in Public)
  • Publishes essays in The Atlantic (with John) on progress studies
  • Funds Arc Institute and Fast Grants as ongoing marketing through philanthropy

Peter Thiel, investor

Work:

  • Plays chess at near-master level
  • Drives one big idea per book, conversation or essay
  • Eats a meat-heavy paleo diet
  • Lives across multiple cities on rotation
  • Returns to René Girard’s work as a fixed re-read

Distribution:

  • Founders Fund and Palantir do the institutional work
  • Published Zero to One (2014) based on his Stanford CS183 lecture notes (Blake Masters compiled them)
  • Sits for one or two long-form interviews a year (Dave Rubin, Stanford, Tucker Carlson, Honestly with Bari Weiss)
  • Hosts the Hoover Institution intellectual circuit

Austin Kleon, writer and artist

Work:

  • Reads a print newspaper every morning and makes a blackout poem from it
  • Walks three miles a day, rain or shine
  • Writes morning pages by fountain pen
  • Reads physical books for an hour before sleep
  • Goes to bed by 9 PM
  • Keeps screens off before 10 AM and after 10 PM
  • Sits for ten minutes of meditation before starting work

Distribution:

  • Sends a Tuesday newsletter every Tuesday for 12+ years
  • Posts daily to his blog at austinkleon.com
  • Workman Publishing publishes the books (Steal Like an Artist, Show Your Work, Keep Going)
  • The blackout poems themselves are public-facing (many originated as social posts)
  • Wrote Show Your Work (2014) as a manifesto for the distribution ritual itself

Pieter Levels, indie founder of Nomad List

Work:

  • Works from a single laptop with no second monitor
  • Codes in cafés instead of offices
  • Lives in a different city every few months
  • Ships one feature or one new product per week
  • Posts live revenue numbers in public
  • Eats one meal a day

Distribution:

  • X (Twitter) is his only marketing channel and he posts to it multiple times a day
  • Posts every product launch, every revenue milestone, every milestone customer
  • Publishes live revenue numbers on nomadlist.com/open
  • Builds in public continuously, with the build-log being the marketing
  • Wrote MAKE (2018) as the indie-hacker handbook that compounded his audience

Tyler Cowen, economist and writer

Work:

  • Reads five or more books in parallel, one per room of the house
  • Drops any book the moment it stops earning its time
  • Eats lunch with a different person each week
  • Travels to a new country several times a year for the food

Distribution:

  • Writes a Marginal Revolution blog post every day, including holidays (since 2003, over 20,000 posts)
  • Writes a Bloomberg Opinion column on cadence
  • Hosts Conversations with Tyler podcast every couple of weeks
  • Funds Emergent Ventures grants (the grant program is also marketing)
  • The daily blog post is the work and the marketing at the same time

Ryan Holiday, writer and bookstore owner

Work:

  • Writes from 8 AM to noon, dressed for the job in jeans and a button-down
  • Journals in two notebooks before any other writing
  • Runs five miles every evening
  • Walks his ranch with his family for three miles when the day ends
  • Reads 100 to 250 books a year
  • Carries a memento mori coin in his pocket at all times

Distribution:

  • Sends a Daily Stoic email every day since 2016 (never missed)
  • Runs The Painted Porch bookstore in Bastrop, TX as a physical marketing artifact
  • Posts annual reading lists
  • Penguin / Portfolio publishes the books
  • Posts to Instagram and YouTube on cadence
  • Records The Daily Stoic Podcast daily

Casey Neistat, filmmaker and founder

Work:

  • Wakes at 5 AM
  • Edits in chronological order without rewinding to fix earlier cuts
  • Skateboards through New York for transit
  • Runs a marathon or longer at least once a year
  • Goes to bed by 10 PM

Distribution:

  • Posted 800 daily vlogs in a row on YouTube (2015-2016). The streak IS the marketing.
  • Sold Beme to CNN for $25M in 2016 and used the news cycle as press
  • Tweets and posts to Instagram daily
  • Runs sponsored content as part of the vlog format, blending product and story

Patrick O’Shaughnessy, investor and podcaster

Work:

  • Reads a physical book every night before sleep
  • Wakes at 5 AM
  • Holds a regular blue-sky half-day for thinking with no agenda

Distribution:

  • Records a new Invest Like the Best episode every week as a forcing function to learn and to market
  • Built the Colossus podcast network on top of the show
  • Sends regular reading recommendations to a private list
  • Writes the annual year-end review

Paul Graham, founder of Y Combinator and writer

Work:

  • Walks while thinking, several times a day
  • Writes by editing his own draft over and over
  • Reads only at night, never during work hours
  • Writes between school drop-off and school pick-up
  • Walks his sons to school every morning
  • Re-reads his own old essays continuously

Distribution:

  • Posts new essays at paulgraham.com sporadically (40-200 over each year of YC’s life)
  • The essays themselves are the marketing for YC
  • Posts on X constantly
  • Y Combinator’s batch system (Demo Day, the network) does the institutional marketing

Tim Ferriss, author and investor

Work:

  • Sits for Transcendental Meditation twenty-one minutes every morning
  • Makes his bed first thing
  • Does five to ten reps of a bodyweight movement before the day starts
  • Drinks “titanium tea” each morning (turmeric, ginger and pu-erh blend)
  • Writes in the Five-Minute Journal for two minutes
  • Takes a two-to-three-minute cold shower or plunge
  • Holds a three-day water-only fast once a month

Distribution:

  • Sends 5-Bullet Friday email every Friday since 2014 (1.5M+ subscribers)
  • Publishes The Tim Ferriss Show podcast on a roughly 2x/week cadence since 2014
  • Writes a year-end review post every January
  • Self-promoted The 4-Hour Workweek (2007) by submitting it to twelve podcast hosts simultaneously, which seeded the podcast era
  • Posts on X and Instagram on cadence

Two daily stacks separate the names you remember from the footnotes you’ve never seen.

What was the first daily ritual you held long enough to compound?

What a Mastermind Group Actually Does

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“You are the average of the five people you spend the most time with.”

Jim Rohn

My first mastermind was in Atlanta.

It was called “Zero to One.” We met at Atlanta Tech Village.

Masterminds do five things you cannot do alone.

1. Ambient Inspiration A mastermind is an environment choice. You are placing yourself inside a room where the default input is people working on hard problems. When people know your goal, they spot connections you miss.

2. External Clarity We see others’ bullshit clearer than we see our own. I failed at my first offer for Trends.vc. Zero bites. I wanted to wait a week to try again. A member named Ash told me: “Pivot now. Be vulnerable. Send the message today.” I did. I made my first $100 in two hours. That $100 broke a three-year streak of zero income. I was blind to the move; he saw it clearly.

3. Accountability “What did you do last week? What will you do this week?” Reporting keeps you on track. You show up because they show up.

4. Talking is Thinking Writing is thinking. Talking is also thinking. Summarizing your week forces you to tell it straight. You cannot solve a problem you cannot describe.

5. The Multiplier Resources. Connections. Once you are on the team, the team is on the lookout. You increase your surface area for luck.

Masterminds meet weekly because long gaps kill momentum. Years with the same people turn weekly reps into trust you can build on.

🌊

Who is scanning the horizon for you?

Charlie Munger’s Learning Machine (In Plain English)

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“Spend each day trying to be a little wiser than you were when you woke up.”

Charlie Munger said this when asked how to live a good life. A wisdom rate. Compounded daily.

Your learning rate is your investment rate. You can’t know which lesson you’ll need until you need it.

I spent three years in a mini retirement reading and thinking with no agenda. Those lessons stayed dormant until I started Trends.vc. Then I wrote 150+ reports on markets. Those lessons stayed dormant too. Now I’m building software businesses and most of them are activating.

When you have the lesson before you need it, the call takes minutes instead of months. Recognition replaces consequence.

Some investors die with money still in the bank. The option to use it was the point.

Of the lessons that activate, a few pay back the whole portfolio. Power-law returns. The big ones are rare.

Aggressive learning compounds only when paired with aggressive action. The shitty fishing pole rule applies. Start fishing while you study fishing.

🧠

What did you learn years ago that’s paying off right now?

Don’t Believe Everything You Think. Test It.

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“Essentially, all models are wrong, but some are useful.”

George E. P. Box

I held a belief for 15 years that meditation had to be the first thing after waking. Then I ran one experiment: sun exposure before meditating. It produced one of the most productive days of the year. Two consecutive days confirmed. A belief that survived 15 years dissolved in 48 hours.

The more experiments you run, the more fit you become to your environment. The more accurate your model of the world. No experiments, no updates. The world keeps moving. The gap widens.

I believed meditation had to come first. The test proved me wrong. Fifteen years of that gap.

More experiments, more fit. Fewer experiments, more wrong.

🧪

Which of your current rules came from a world that no longer exists?

5 Things Chess Teaches Us About Life

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“The game of Chess is not merely an idle amusement. Several very valuable qualities of the mind, useful in the course of human life, are to be acquired or strengthened by it, so as to become habits, ready on all occasions.”

Benjamin Franklin, “The Morals of Chess” (Columbian Magazine, Philadelphia, December 1786).

I sat down to play one game of chess. One game became two. Two became a dozen. Twelve hours later the day was gone.

The newest version of the app felt built for exactly that. A fresh opponent loads the second a game ends. Win or lose, one game flowed into another. So I deleted the app.

Chess taught me a lot anyway. Five of its lessons run my work and my life.

  1. Alignment. You write a book. It brings speaking invitations. Those talks sharpen your ideas into the next book. Its readers were waiting before you finished it. A chess position works the same way. The strongest single piece rarely wins it. The pieces that guard each other and attack together do.

  2. Compensation. A grocery store sells milk below cost, on purpose. The cheap milk pulls shoppers through the door and they fill a cart on the way to the fridge. Chess calls that trade compensation: you give up a pawn or a piece and get a faster attack, more space or better squares in return. Material goes down. Position goes up. Off the board you pay with money, time and focus. The question worth asking is whether the position is worth it.

  3. Force ranking. Your to-do list has ten items, all marked high priority. When each task is top priority, none is, so you drift to whatever’s loudest or easiest. Chess won’t let you do that. You get one move per turn. Three or four moves might look strong, so the game forces you to compare them head to head and commit to one. Force rank your list the same way: task one against task two, the winner against task three, until one survives the whole list.

  4. Position over material. One person earns far more than the other and can’t quit: the mortgage, the car and the tuition are all sized to that salary. The other earns less and walks away whenever she wants. Chess trains the same eye. You can hold more pieces than your opponent and still get checkmated, because a safe king and active pieces beat a bigger pile of material. Where your pieces stand is your position. Off the board, position is your options, your freedom to move and who you answer to.

  5. The clock. A cook hits a dinner rush. Twenty orders are up at once. Ten minutes spent perfecting one plate is ten minutes the other nineteen tables wait. Speed chess runs on a three-minute clock. Players lose more games to the clock than to a bad move. The best move on the board is worthless at zero seconds. Work has a clock too, even when you can’t see it.

Games are teachers that some of us mistake for toys.

♟️

What game has taught you the most about life?

Build Systems So Your Work Runs on Easy Mode

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“Doing more and more with less and less.”

Buckminster Fuller

I draft most posts on walks.

Each post used to take hours at a desk.

That changed with one experiment. I set up voice-to-text.

I walk every day either way. The draft happens during the walk.

An experiment is anything you do that is uncertain or uncomfortable. An infrastructure experiment is one that leaves you with a new capability.

Voice-to-text was an infrastructure experiment.

Leverage is your outcome divided by the energy you put in. A post is an outcome. Talking while I walk costs almost no added energy. I get more leverage on every post.

⚙️

What’s one capability you could build that makes every future task cheaper?

We Are All Investors

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“The cost of a thing is the amount of what I will call life which is required to be exchanged for it, immediately or in the long run.”

Henry David Thoreau

Say the word investor and most people picture money. Stocks, real estate, a portfolio climbing on a screen.

That’s one kind of investor. Money is one resource.

You also hold awareness, environment, attention, willpower, energy and time. Money sits at the bottom of that stack.

There’s a gap between where you are and where you want to be. You close it through trades. Each trade spends one resource to buy another.

Most people make those trades blindfolded. They say yes to a meeting and skip the question of what the hour costs. They check email ten times a day and skip the question of what they bought with the speed.

A conscious investor asks first.

  • What am I spending?
  • What am I buying?
  • Is the return worth it?

Here’s one trade I made recently. I went from two operations days a week to one. I trade slower email replies for six days of unbroken attention.

Look at where you are. Look at where you want to be. Each step between the two is a trade.

🤝

“What trade have you been making without calculating the return?”

The Optimization Trap That Broke My Meditation Habit

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“I almost never get the question: ‘What’s not going to change in the next 10 years?’ And I submit to you that that second question is actually the more important of the two. Because you can build a business strategy around the things that are stable in time.”

Jeff Bezos, 2012

I broke my meditation practice many times over fifteen years.

Each time, it started the same way. The practice was working well. So I started poking at it. Maybe I could shorten it. Maybe I could substitute something more efficient.

Then things fell apart.

  • Anxiety crept back
  • Sleep degraded
  • Decisions got worse

The gap between the change and the consequence was one to two weeks. Long enough that I attributed the decline to something else.

I took the benefit for granted because the practice was working. And the time invested looked easy to trim because it took time I wanted for other work.

That’s the optimization trap. A working system you’ve stopped crediting. A small change you make to try to ‘improve’ things. A feedback loop that’s delayed enough that you blame it on something else.

The defense I built is to take a religious-like approach to certain habits. Once I’ve seen enough, I stop touching them. I’ve been burned too many times.

Hard to vary means I stop debating it each day. The question shifts from “is this worth doing today?” to “it’s time.”

I stopped treating these practices as habits to optimize. I started treating them as prerequisites for everything else.

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What’s the last working thing you broke by trying to improve it?

How to Get Out of Your Comfort Zone, Faster

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“We make our world significant by the courage of our questions and by the depth of our answers.”

Carl Sagan

I run at least 55 experiments a day.

  • Some drain me
  • Some light me up
  • Some change everything that comes after them

An experiment is anything new and/or uncomfortable. Three types cover most. Two attributes give some extra weight.

Mental experiments involve your mind. Meditate. Read a book you disagree with (or think you do). Test a new mental model. Challenge a belief you’ve held for years.

Physical experiments push your body. Run. Lift. Cold plunge. Change how you eat.

Social experiments involve other people, reputation or public exposure. Send a Notion document to eight founders before writing code. Publish a post. Ask for feedback in a mastermind. Cold outreach to someone you admire.

For me, mental experiments are easiest. They give me energy. Physical experiments sit in the middle. Social experiments cost me the most. Processing social signals drains me.

For an extrovert the ranking might flip.

Five years ago, social experiments cost me more than they do now. The more I ran, the easier the next one became. Reps reduce anxiety.

Some experiments carry extra weight. Two attributes worth watching.

Infrastructure experiments make other things possible or easier. Setting up a daily cron job. Building a deployment pipeline. Creating a reusable template. The output stays in the system and shows up in every experiment that comes after.

Removal experiments take something away to see if the system still works without it. Cut a meeting. Drop a tool. Archive a habit you’ve outgrown. If the system holds up, the removal is permanent. The gain compounds every day you’re free of the thing you removed.

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Which type of experiment costs you the most energy?

Why I Rewrite My Principles by Hand

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I write entirely to find out what I’m thinking, what I’m looking at, what I see and what it means.

Joan Didion, “Why I Write,” 1976

Each day I’d open my notebook and copy yesterday’s principles to a new page by hand. Some lines I wrote without thinking. Others slowed me down.

Then I moved my principles to a digital list. I barely opened it. The friction and engagement were gone.

The daily rewrite was doing more work than I knew. The repetition kept those principles in front of me. It was also meaningful friction that surfaced what was still worth rewriting.

Call it natural selection on your ideas. Rewriting acts as selection pressure. Strong ideas stay. The rest fall away.

This is how I built my rules. The same logic shapes my experiments list.

A digital list lets old ideas that are no longer relevant sit around. The rewrite shows you which are still worth holding onto.

✍️

What do you believe enough that it’s worth rewriting daily?