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Paul Graham's Essays Part II

What I learned from reading Paul Graham’s essays (http://www.paulgraham.com/index.html) https://www.founderspodcast.com/ Full Transcript and Show Notes: https://www.founderspodcast.com/episodes/91666180/senra-paul-graham-lessons-from-his-essays-pt2 David Senra: https://x.com/FoundersPodcast?s=20

David Senrahost
Dec 8, 202349mWatch on YouTube ↗

CHAPTERS

  1. 0:00 – 3:23

    Founders Notes: A Readwise Product for Founders

    David Senra explains how Readwise became central to his work and how he partnered with its founders to build foundersnotes.com. It gives subscribers search, a highlights feed, and his favorited highlights, and is aimed at founders already running successful companies.

    • •Senra has over 20,000 highlights and notes from more than 300 books in Readwise
    • •People kept asking for access to his Readwise, which led to the partnership
    • •Subscribers can search by book and keyword, use the highlights feed, and see his 839 favorites
    • •It is yearly-only and priced at half its eventual price at launch
    • •Intended for founders already running successful companies
  2. 3:23 – 8:36

    How to Think for Yourself: Independent-mindedness and Curiosity

    Senra reads Paul Graham's essay on independent thinking. Graham argues that some work requires ideas that are both correct and novel, that independent-mindedness is more nature than nurture, and that surrounding yourself with independent thinkers helps. He ties it to curiosity, saying one should do what one is curious about.

    • •Startup ideas that sound bad but aren't, like Microsoft and Airbnb
    • •Conventional-minded people don't see themselves as conventional
    • •Founders can speak more freely with other founders than with their own employees
    • •Read history and avoid intellectual fashions
    • •Motto: do what you're curious about, not just what you love
  3. 8:36 – 13:52

    How to Work Hard: Talent, Practice, and Effort

    Senra begins Graham's essay How to Work Hard after noting he is sick. Graham says great work requires natural ability, practice, and effort, with Bill Gates, Messi, and P.G. Wodehouse as examples. Senra adds Graham's reply to Patrick Collison and Rick Rubin's view on doing more to get less.

    • •There is no way to evade hard work through sheer brilliance
    • •Graham called the idea of building Stripe without hard work an empty set
    • •Three ingredients: natural ability, practice, and effort
    • •Gates took no day off in his 20s; Wodehouse rewrote sentences 10 to 20 times
    • •Rubin: less is more, but you have to do more to get less
  4. 13:52 – 17:47

    Fire in the Belly: Discomfort with Idleness and Finding Your Limit

    Graham describes alarm bells going off when he isn't working hard and how he stopped watching TV at 13. Patrick Collison dates his own distaste for idleness to 13 or 14, and school was the biggest obstacle to seeing real work. Graham says his limit is about five hours a day for hard writing or programming but not when running a startup, and that you find your limit only by crossing it.

    • •Not working feels awful to Graham, a gift and a curse that Senra says should be moderated
    • •Graham stopped watching TV at 13; Collison had a similar moment at 13 or 14
    • •School made work seem boring and pointless
    • •Limits differ by type of work
    • •The only way to find your limit is to cross it, and honesty is needed in both directions
  5. 17:47 – 20:39

    Fear, Flaws, and Aiming at the Hard Core of Problems

    Graham says what drives him depends on the work: fear of failure at Viaweb, and the flaws in his essays now. Senra connects this to Jimmy Iovine using fear as a tool. Graham advises aiming at the hard core of a problem rather than the easy edges.

    • •Fear of failure drove Graham at Viaweb, with almost no procrastination
    • •Jimmy Iovine described wrestling fear so it pushes you from behind
    • •Flaws in essays now drive Graham to keep working
    • •Many problems have a hard core surrounded by easier edges
    • •Aim as close to the center as you can without stalling
  6. 20:39 – 25:16

    Interest as the Guide: Choosing What to Work On

    Graham says consensus about which problems matter is often wrong, and ambitious work that is easier for you is a bargain. He says a deep interest makes people work harder than discipline can. He compares Mozart and Newton and says interest is the best test. Graham closes by calling hard work a complicated, dynamic system that honesty tunes.

    • •The consensus on important problems is often mistaken
    • •Some of the best work is done by people who find an easy way to do something hard
    • •Deep interest beats discipline, and Senra also links this to Naval
    • •Most people follow a Newton-like path rather than Mozart's
    • •Interest is the best test of whether work is worthwhile
    • •Working hard is a dynamic system, not a dial turned up to 11
  7. 25:16 – 29:26

    How to Lose Time and Money: Fake Investments and Fake Work

    Senra moves to Graham's 2010 essay on how fortunes are lost, which says it is mostly through bad investments rather than spending. Calling something an investment bypasses our alarms about spending. Graham says time works the same way, with fake work bypassing the alarms that idleness would set off.

    • •Most fortunes are lost through bad investments, not excessive expenditure
    • •Senra recalls athletes going bankrupt through bad investments like lending money to relatives
    • •Calling a purchase an investment bypasses spending alarms
    • •Fake work like email bypasses the alarm that idleness triggers
    • •The worst traps mimic virtuous behavior and are not even fun
  8. 29:26 – 32:42

    Schlepp Blindness: Why Hard Problems Are Opportunities

    Senra reads Graham's essay on schlepp blindness, the unconscious avoidance of tedious, unpleasant tasks that hides startup ideas. Stripe and payments serve as the main example. Hard ideas face less competition, and Graham suggests ignorance and asking what problem you wish someone would solve for you.

    • •A company is defined by the schlepps it will undertake
    • •Your unconscious hides ideas that involve painful schlepps
    • •Stripe fixed a problem many hackers knew was painful
    • •Ambitious ideas are like undervalued stocks with less competition
    • •Ignorance is the antidote; ask what problem you wish someone else would solve for you
  9. 32:42 – 37:22

    What I've Learned From Users: Recurring Startup Problems

    Senra introduces Graham's 2022 essay on lessons from Y Combinator startups. Graham says startups tend to have the same problems, and Senra shares a tweet about a profitable nine-person startup. Founders are often bad at identifying their real problems or ranking them, such as when investors can tell a company is doing badly.

    • •Most startups have the same problems, but each is unique and advising can't be a formula
    • •Graham's tweet about a profitable nine-person startup growing 20x a year
    • •Founders often mistake the symptom for the problem, like fundraising difficulty
    • •Asking whether you'd use the product if you hadn't built it, which Senra links to Steve Jobs
    • •Founders often miss which problem will kill the company, like ignoring the ajar door in a horror movie
  10. 37:22 – 38:33

    Why Founders Don't Listen: Counterintuitive Startups

    Graham says a big surprise at YC is that founders often don't listen, and they come back a year later wishing they had. The reason is partly stubbornness but mostly that so much about startups is counterintuitive. Senra ties this to Charlie Munger's idea of studying histories of 100 companies.

    • •Founders return a year later and say they wish they'd listened
    • •Counterintuitive advice sounds wrong to the person hearing it
    • •Munger would teach business through the histories of 100 companies
    • •No one knows what it's like except those who've done it
    • •Senra says he would likely make the same mistake and tries to pause and step outside himself
  11. 38:33 – 42:30

    Focus, Speed, and Course Correction

    Graham advises founders to find the most important problems, try solutions, and correct course frequently, being decisive at a micro scale and tentative at a macro scale. Senra connects this to Bezos's two-way doors and "shoot, shoot, shoot, and then aim." Graham says speed defines startups and focus enables speed.

    • •Focus matters doubly for early-stage startups, which have few people
    • •Correct course often to be decisive at a micro scale and tentative at a macro scale
    • •Bezos's one-way and two-way doors, and shooting before aiming
    • •Running back metaphor for a winding but fast path
    • •Speed defines startups, focus enables speed, and YC improves focus
  12. 42:30 – 45:31

    Colleagues, Clusters, and Founder Generosity at YC

    Graham says the other big thing YC gives founders is colleagues, because great work clusters around certain places and ambitious people are starved for peers. Senra jokes it is Warren Buffett-level content marketing. He closes with Graham's point that founders are generous in helping one another and previews the Hackers and Painters episode.

    • •Great work clusters around certain places and institutions
    • •Ambitious people need colleagues more because they lack them in everyday life
    • •YC was designed to be what Graham wanted when he was starting a startup
    • •The energy at a YC dinner is unlike anything else
    • •Founders' generosity in helping one another is the happiest thing Graham learned
  13. 45:31 – 49:30

    Founders Notes Features Walkthrough

    After the episode ends, Senra walks through the foundersnotes.com features he uses most: search, the highlights feed, books, and favorites. He gives examples such as searching hiring and reading randomized highlights from Buffett, Catmull, and a biography of Alibaba. He repeats that it is for founders running successful companies and suggests trying it for a year.

    • •Search highlights by keyword, such as hiring
    • •The highlights feed shows randomized tweet-sized highlights
    • •The books view lets you reread highlights from a single book, like Bloomberg's autobiography
    • •Favorites hold his 839 saved highlights
    • •Recommended as a year-long test for founders already running companies

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