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Letter to Paul Graham: Learning to See
Mar 1600:17:53Tap to summarizePaul Graham is known as a programmer, essayist, and cofounder of Y Combinator. But alongside all of that, he is a painter - studying still lifes at RISD and the Accademia di Belle Arti in Florence, learning to override his brain's shortcuts and see what was actually there."You feel as if you're an animal in its natural habitat. Doing what you were meant to do. Not always happy maybe, but awake and alive." Paul GrahamThis Craftsmith Letter traces a single skill - the painter's eye - through everything Paul has worked on: Lisp, Viaweb, his essays, Y Combinator, and a decade of writing about how to find work you love. The letter is also an invitation; Paul, if anything here rings true, let's record an episode together.In this letter:How painting still lifes in Florence taught Paul to see past abstractionsThe "garage sale test" - strip away prestige to find what's realHow Paul applied the garage sale test to everything he worked onWhy interest is more unevenly distributed than abilityThe traps that steer you away from following your authentic curiosity"Always produce" as a heuristic that finds your life's workWhy most great work starts as a projectWhat it actually feels like to do work you loveChapters:(00:00) - Intro (00:18) - How YC Changed VC (01:47) - The Painter’s Eye (02:46) - Seeing Past Shortcuts (04:12) - Garage Sale Test (04:50) - Lisp and Clear Structure (05:35) - Viaweb and Web Apps (06:09) - Essays That Reveal Reality (07:21) - YC Origins and Insight (08:37) - Few Find Work They Love (09:07) - Interest Beats Ability (10:36) - Prestige Versus Curiosity (11:35) - Doctor Story and Traps (12:37) - Always Produce Heuristic (13:19) - Follow Curiosity, Do Projects (14:42) - Doing Great Work Mindset (16:10) - What Work You Love Feels Like (17:09) - Weekly Challenge References:"What I Worked On" — Paul Graham"How to Do Great Work" — Paul Graham"How to Do What You Love" — Paul Graham"The Bus Ticket Theory of Genius" — Paul Graham"How to Get Startup Ideas" — Paul GrahamOn Lisp — Paul Graham (book)Help deliver this letter:Paul is @paulg on X. Send him this episode and help it reach him.Follow Craftsmith:Apple PodcastsSpotifyYouTubeCraftsmith is a podcast by Bill Allred about people doing work they love, so you can too.
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Letter to Bill Gurley: Five Fascinations
Mar 900:22:59Tap to summarize"I couldn't discover something that got me excited. Slowly, I've come around to an idea that I made up. It's not a career that other people have." - Bill Gurley to Tim FerrissBill Gurley's first principle is "find your passion." But how did Bill actually find his? He didn't have one passion - he had five fascinations pulling in different directions. A love affair with technology, a gambling bug, a deep curiosity about markets, a need to write, and a desire for wealth. Most people would pick one. Bill held all five, with no idea how they'd fit together - and kept building until they did.This is a Craftsmith Letter, an audio letter to a living craftsperson.In this letter:How growing up on a street of NASA scientists in Dickinson, Texas shaped how Bill learned to thinkThe moment his sister's stock options at Compaq showed him a different kind of wealthWhy Bill was "surprisingly bored" at one of the most exciting companies in techThe Palm Pilot move: how he spammed 350 of the most powerful people in tech with his newsletterFrank Quattrone's question that changed everything: "What is your dream job?"The 10:30 PM walk on the 36th floor of Park Avenue Plaza - and the question he asked himselfWhat Bill told Tim Ferriss that reveals the pattern of his entire career: "I made it up. It's not a career that other people have."Why boredom isn't ingratitude - it's data about which fascinations aren't being servedChapters:(00:00) - Why This Letter (00:28) - Bill Gurley’s Big Idea (01:21) - Five Fascinations (02:31) - NASA Roots in Texas (03:48) - Sister’s Compaq Spark (05:07) - Gambling Bug Awakens (06:06) - Writing as Thinking (07:47) - Bored at Compaq (09:23) - MBA and VC Dream (10:19) - Wall Street Detour (11:34) - Palm Pilot Power Move (12:54) - Silicon Valley Breakthrough (13:15) - Boredom Returns Again (14:21) - Finally Venture Capital (16:46) - Permission to Fail (17:28) - Post-Benchmark Restlessness (18:34) - Make It Up Again (19:45) - Lessons on Boredom (20:56) - The Book Needed Permission (21:57) - Invitation and Next Steps (22:07) - Weekly Exercise and Share References:Runnin' Down a Dream by Bill GurleyBill Gurley's UT Austin talk - the original "Runnin' Down a Dream" speechAbove the Crowd - Bill's blogSource conversations referenced in this letter:Bill Gurley on Tetragrammaton with Rick Rubin - where Bill discusses permission and disinhibitionBill Gurley on The Tim Ferriss Show #840 - where Bill reveals "I made it up"Help deliver this letter:If you think Bill should hear this, send him this episode:@bgurley on XBill Gurley on LinkedInFollow Craftsmith:Apple PodcastsSpotifyYouTubeCraftsmith is a podcast by Bill Allred about people doing work they love, so you can too.
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Letter to Steve Martin: Obsessed by Making
Jan 2400:18:06Tap to summarizeIn 1977, Steve Martin played Nassau Coliseum to 45,000 people - the biggest concert comedy event in the history of show business. He reached this peak despite having, in his own words, "no natural talent". And then he just walked away. He didn't perform stand-up again for decades. Why would anyone at the pinnacle start over from zero in film, writing, and music? The answer was hiding in the very next line of a poem he spent a decade trying to understand.This is a Craftsmith Letter, an audio letter to a living craftsperson.In this letter:The line from E.E. Cummings that Steve puzzled over for ten years - and the next line he never mentionsWhy watching Wally Boag hundreds of times at Disneyland was Steve's first masterclassThe moment a magician's failed trick taught Steve that laughter could come from absenceWhat Steve's father said on his deathbed, and the more complicated truth Steve kept to himselfThe Bird Cage Theater: 4,000 performances that became a laboratory for breaking comedy's rules"What if there were no punch lines?" - the question that changed everythingThe Vanderbilt swimming pool moment: when the audience wouldn't leave and Steve became the actWhy the banjo is the control group that proves the thesisChapters:(00:00) - Introduction to Craftsmith (00:08) - A Letter to Steve Martin (00:23) - Steve Martin's Journey to Mastery (01:20) - The Philosophy of Mastery (03:23) - The Influence of Early Mentors (05:57) - Breaking the Rules of Comedy (08:05) - The Road to Becoming (14:32) - The Banjo: A Lifelong Passion (15:27) - The Wisdom of Making (17:22) - Conclusion and Invitation Books mentioned:Born Standing Up by Steve MartinSix Nonlectures by E.E. CummingsHelp deliver this letter:If you think Steve should hear this, send him this episode:stevemartin.com@stevemartinreally on Instagram@SteveMartinofficial on FacebookFollow Craftsmith:Apple PodcastsSpotifyYouTubeCraftsmith is a podcast by Bill Allred about people who discover and develop work they love, so you can too.
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Letter to Steven Pressfield: Naming the Creative Enemy
Jan 1600:19:08Tap to summarizeWhy did a late bloomer who didn't publish his first novel until 52 become the definitive voice on creative resistance? Because fought it hand-to-hand for 27 years, and every chapter of The War of Art traces back to a battle he lived.This is a Craftsmith Letter - an audio letter to a living craftsperson.In this letter:A typewriter carried for years but hated too much to openWhy he pulled the pin at 99.9% done again, and againA bumper sticker that planted the seed for an entire bookThe most honest thing anyone's said about not giving upThe night he sat down crazy and got up saneBooks mentioned:The War of Art by Steven Pressfield Govt Cheese by Steven PressfieldTurning Pro by Steven PressfieldPut Your Ass Where Your Heart Wants to Be by Steven PressfieldThe Legend of Bagger Vance by Steven Pressfield Help deliver this letter: If you think Steven should hear this, send it to him. Website: stevenpressfield.comX: @spressfieldInstagram: steven_pressfieldFollow Craftsmith: Apple Podcasts | Spotify | More Craftsmith is a podcast by Bill Allred about people who discover and develop work they love, so you can too.
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