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Lehman Brothers and the Pull of the Opportunistic Path
The host recounts a Lehman Brothers play about a family that went from selling fabric to becoming a bank. He ties it to his own habit of choosing money-making pit stops over the more fulfilling path.
- •Lehman's rise from fabric store to cotton middleman to investment bank
- •The line that for the bank 'our flour is money'
- •Once financialized, the firm never went back, ending in the 2008 collapse
- •The host admits repeatedly choosing opportunistic pit stops over fulfilling work
- •Sam frames the choice as art versus money
The War of Art: Resistance and the Unlived Life
The host explains how a screenshotted passage from The War of Art led him to read half the book. He describes the idea of resistance and the difference between an amateur and a pro who shows up daily.
- •Most people have the life they live and an unlived life within
- •Resistance is described as more powerful than a locomotive and harder to kick than crack
- •The host felt inspired rage rather than sadness
- •The pro shows up every day whether or not they feel like it
- •Doing the work daily turns three lines into pages and eventually into your best work
Jerry Seinfeld's Daily Work and the Glenn Miller Parable
Sam brings up how Jerry Seinfeld gets tactical about writing a bit every day even when it's garbage. A clip is then discussed in which Seinfeld tells a struggling comedian a parable about musicians trudging through the snow while envying a family in a warm house.
- •Seinfeld writes jokes with a pen and yellow notebook for about an hour a day
- •Most of what he writes is garbage, but he does it anyway as his job
- •Seinfeld tells a struggling 29-year-old that his friends' progress has nothing to do with him
- •The Glenn Miller parable: musicians in the snow envy a cozy family
- •True artists choose discomfort while doing exactly what they want
Brett Adcock: Telling Yourself a Story About Your Work
Sam recalls telling the host a company doesn't have to save the world, then describes how Brett Adcock framed his earlier job-board company as meaningful because of the time it takes from your life. Sam then lays out how Adcock moved on to Figure and a school-weapons detection company.
- •Sam earlier argued a company can be about creating good jobs rather than saving the world
- •Adcock said you spend 40-50 hours a week away from family, so it should be something you enjoy
- •Adcock chose between lab-grown meat, robots and NASA-derived weapon detection
- •He cold-called the NASA researcher, licensed the tech and put $10 million into cover.ai
- •Sam felt his own 'it doesn't have to save the world' line may have been a cope
One-Chart Businesses and Why Big Missions Are Easier
The host connects Adcock's pitch to the idea of one-chart businesses, where a single chart justifies the venture. Sam adds Adcock's view that big missions make recruiting employees, investors and customers easier.
- •A one-chart business can be explained with one chart, like the rise of cremation
- •D2C brands could have been explained by time spent and CPMs on Facebook
- •Adcock pulled up a school-shootings-per-year chart as his pitch
- •Adcock said he feels compelled to take on the problem
- •Adcock told Sam big things are in many ways easier because the mission attracts people and money
"What Would I Do If I Wasn't Afraid?"
The host says his takeaway isn't that everyone must solve a gnarly problem. Instead the better question is what you would work on without fear of failure, and he separates your choices from outcomes, citing Rick Rubin.
- •Ask 'What would I do if I wasn't afraid?' instead of 'What should I do?'
- •Fear of failure or of it being too hard stops people, whether it's robots or a creative project
- •Control what you can control: the time and effort, not the outcome
- •Rick Rubin's view that you don't make 'popular', you just make a lot of stuff
- 23:27 – 30:10
Sylvester Stallone and the Wolf at the Door
The host recounts Stallone's 1970s interviews about writing Rocky with $106 in the bank and turning down offers of up to $265,000 unless he played Rocky. Stallone said the opportunity to find out whether he was living a lie mattered more than money.
- •Stallone wrote the script in three and a half days with the wolf at the door
- •He refused offers up to $265,000 because he insisted on playing Rocky
- •Rocky was made for about $960,000, with Stallone paying himself SAG minimum
- •He said he'd have done it for a donut and a tuna fish sandwich
- •He didn't want to be 50 and a creative person who never did anything creative
Stallone's Speech Adversity and Riffing on Sly
The hosts gush over Stallone as a new crush. The host explains that nerve damage from forceps at birth left part of his face paralyzed, causing people to assume he was dumb despite being well-read and a skilled writer.
- •The hosts joke that Stallone is their new crush
- •Forceps at birth damaged a facial nerve, affecting his speech
- •People assumed he was dumb because of his build and slur
- •He was well-read and wrote the Rocky script
- •The host plans a separate YouTube video as an homage to Stallone
Low Key Billy: Michael Pryor's Fishing Trip
Sam tells of being invited fishing by Michael Pryor, whom he met in Hampton. Pryor co-founded Fog Creek Software and spun off Trello and Stack Overflow, and he now spends his days fishing.
- •Pryor lives in a large waterfront home near New York City
- •Fog Creek spawned FogBugz, Trello and Stack Overflow
- •Trello sold to Atlassian for about $450 million and Stack Overflow for about $1.8 billion
- •Pryor was a programmer who learned to be CFO as the company needed it, and said he wasn't intense
- •His partner Joel writes the blog Joel on Software
- •The boat made the fishing easy, and Sam caught a three-foot fish
Being Popular vs. Being Rich
The host asks what Pryor was curious about, and Sam says low-key wealthy people are curious what it's like to have an audience. Sam says he would trade his audience for their net worth any day, since the audience mostly means typing tweets from his bedroom.
- •Rich, low-key people are curious what having an audience is like
- •Sam would trade his audience for a bank account any day
- •He describes the work as typing tweets in his bedroom or on the toilet with little joy
- •Sam thinks the audience isn't actually enviable
The Price to Never Create Content Again
The host asks what it would take to stop publishing forever. Sam says $30 million, while the host first says $250 million and then walks it back to account for expecting to earn that anyway and liking the work.
- •Sam's number is $30 million
- •The host first says more than $100 million, then settles on $250 million
- •Sam accuses the host of being full of it and not being Rocky
- •The host says the number must cover lost future earnings and enjoyment, plus the time value of upfront money
- •Sam says a pen-name loophole would raise his number
Pen Names, Kal Penn and Leonardo DiCaprio
The conversation drifts to pen names and stage names. They cover Jack Carr, Kal Penn's name change to get auditions, and Leonardo DiCaprio refusing to become Lenny Williams, before wrapping the episode.
- •Sam is fascinated by authors who use pen names, like Jack Carr
- •Kal Penn changed his name from Kalpen Suresh Modi to get auditions
- •Many actors, including Mindy Kaling, changed names
- •Studios wanted DiCaprio to be Lenny Williams and he refused
- •The hosts wrap up the podcast
Publisher timestamps
- 0:00The rise and fall of the Lehman Brothers
- 4:56The life we live vs the unlived life
- 9:13How Jerry Seinfeld puts in the work
- 12:54You don't have to save the world
- 21:45“What would I work on if I wasn't afraid?”
- 30:10Low Key Billy of the Week: Michael Pryor
- 39:29Sam reflects on being popular
- 40:58Sam and Shaan's "number" to walk away
