Sam Parr is a copywriter, entrepreneur, and media company builder who founded The Hustle (a daily business newsletter that grew to nearly 4 million subscribers before being sold) and now runs Hampton, a community for high-growth founders and CEOs. This episode is a deep dive into how Sam thinks about writing, copy, media, and building companies—centered on the idea that writing is the most undervalued skill in business because it forces clear thinking and gives the writer invisible power to set the frame for how communities and companies operate.
The Core Insight That Started The Hustle
Sam realized that the math of email was radically different from web traffic: if you get a million subscribers and email them daily with a 50% open rate, that’s 15 million reads per month—enough to generate roughly $2 million in revenue.
At the time (around 2014), no one took email newsletters seriously; they were dominated by financial advice sites and shady affiliate operations. Sam saw an opportunity to blend direct-response copywriting with journalism.
He launched The Hustle in 2016, and growth was rapid: 150K subscribers in year one, 500K in year two, 1 million in year three, and 1.7 million by the time of sale.
How Sam Wrote Viral Content
His strategy was to go where his target audience already gathered (like Reddit subreddits) and siphon them off. He’d identify a subreddit—like self-publishing—and create content designed to go viral there.
One early stunt: he wrote about a guy making $60K/month by scraping content from books about how to sleep with women, repackaging it with a sexy title, and gaming Amazon’s Kindle rankings with fake reviews.
Sam then one-upped it: he plagiarized an existing romance novel, changed the title to something absurd (a werewolf Navy SEAL), bought fake reviews, and hit #1 in its category—proving Amazon’s rankings couldn’t be trusted. The publisher threatened to sue; Sam framed it as investigative journalism.
Another viral hit: he had someone live on Soylent (the meal replacement) for 30 days and posted it in the Soylent subreddit. The colloquialism “Slim Fast for nerds” came from this era.
These stunts drove millions of visits and converted readers into newsletter subscribers through a popup with cheeky copy: “If you don’t like it, we’ll bill you a dollar.”
The AIDA Framework
Sam structures all transactional copy using AIDA: Attention, Interest, Desire, Action.
Example: instead of saying “drink more water,” you’d say: “Have you seen those beefy guys at the gym carrying gallon jugs of water? (Attention) Studies show water builds muscle 30% faster. (Interest) If you drink eight glasses a day, you’ll gain muscle faster and your skin will look great. (Desire) Buy our water bottles. (Action)”
He applied this to popups, footers, and onboarding emails—every piece of “forgotten text” had to earn its place.
Onboarding Emails as “Forgotten Text”
Most companies treat the thank-you page and welcome email as an afterthought. Sam saw it as prime real estate.
His welcome email for The Hustle was a vivid, over-the-top narrative: “A bell went off in our office when you signed up. My head of operations ran outside and hugged a stranger. John is doing 15 push-ups to burn off the excitement. I have to go stop them before they get in trouble—but first, thank you.”
The brand at the time was “a little bro-y,” so the obnoxious tone worked. The principle: every touchpoint must be crafted, not defaulted to.
Researching Other Companies’ Copy
Sam’s key advice: don’t look at what successful companies do now—use the Wayback Machine to see what they did in their early days.
When they were small, they had to make every word count. Once they’re big, committees add complexity and dilute what worked.
Example: Morning Brew’s original homepage was just an email input field. Now it looks like every other media site because committees decided to copy GQ.com. The Hustle did the same thing after selling.
The lesson: study the scrappy version, not the mature version.
Counter-Positioning Against New York Media
Sam’s meta-strategy for starting media companies: look at how New York media covers a space, then do the opposite.
Ben Thompson (Stratechery) analyzed tech business models while traditional tech media just reported gadgets. Barstool Sports went after pizza bros while ESPN wore suits behind desks.
The pattern: find the sterile, homogeneous approach and offer something with personality that reaches the audience being ignored.
Sam’s Writing Influences and Taste
He reads roughly one book a week, mostly history and narrative non-fiction. He’s drawn to stories of extreme hardship (Lewis and Clark, shipwrecks) because they make his own challenges feel manageable.
He admires simple, direct language: Hemingway, J.D. Salinger, and Robert Caro. Great writing at a fifth-grade reading level can still carry deep meaning.
He’s obsessed with phrasing—how words sound and feel. His favorite writers for this: Scott Galloway (rhythmic, lyrical, funny), Felix Dennis (author of How to Get Rich, who writes like “Richard Branson and Mick Jagger had a baby”), and Neville Medhora (his best friend and a copywriter who makes him happy to read).
He also loves Anthony Bourdain for boldness, David Foster Wallace and Gregory David Roberts (Shantaram) for hyper-descriptive writing that feels “more real than real.”
Robert Caro and the Discipline of Research
Robert Caro, the biographer of Lyndon Johnson, moved to the Texas Hill Country for two years to interview people in person because phone interviews weren’t working. His mantra: “Make me see the scene.”
Sam visited Caro’s ranch and read the biography while looking at the actual landscape Caro described—seeing how precisely Caro rendered physical details.
From Nick Bilton’s American Kingpin (about Ross Ulbricht and Silk Road): Bilton reconstructed the scene of Ulbricht’s arrest by checking weather records for wind direction, analyzing Facebook photos for shadows, and reading Ulbricht’s daily diary entries. Sam was stunned by the rigor.
The Ethics of Non-Fiction Storytelling
Sam believes most narrative non-fiction writers “fudge” small details to make stories more cohesive—not lying, but omitting or compressing.
Example: a Korean War book describes a soldier closing a door and thinking specific thoughts. The author wasn’t there, but the soldier probably thought something like that at some point. It’s not a lie; it’s storytelling.
His rule: you can leave out the three other people in the car if they don’t matter to the story. Every sentence should serve the narrative.
Copy Work: How Sam Learns to Write
Copy work is the practice of handwriting (pen and paper, not typing) great writing by other authors to internalize rhythm, texture, and structure.
Ben Franklin did it. Hunter S. Thompson retyped The Great Gatsby to feel what it was like to write a great novel. Jud Apow did it with SNL scripts.
Sam did “copy hour” for months: one hour per day, hand-copying the best sales letters ever written. He still does 10 minutes before writing sessions—copying, say, Anthony Bourdain when he needs boldness.
The principle: just as musicians learn by playing other people’s songs, writers learn by copying other people’s prose before developing their own voice.
Building a Writing Team at The Hustle
Sam hired people who weren’t professional writers: Trung worked at an analytics company, Steph was a product manager, Zach was a blogger. He found them by looking at the “bottom fourth of their resume”—hobbies, sports, random interests—and seeing if they could tell him an entertaining story about it.
If you spent $200K on college and can’t entertain me about your favorite class, that’s a red flag.
He also looked for people writing for fun (personal blogs, Twitter). Steph was hired because of a single headline on her blog: “To be great, just be good consistently.”
Onboarding: new hires had to rewrite The Hustle’s daily email by hand for a few weeks to internalize the voice, then they were set loose.
The Two Lengths That Work
Sam’s rule: write either fewer than 500 words or more than 2,000 words. The middle ground is “no man’s land.”
Short pieces work for quick, shareable content in the flow of someone’s day. Long pieces work for intentional, sit-down reading.
Zach Crockett, The Hustle’s best writer, consistently produced viral Sunday stories—either very short or very long. He was “the Lady Gaga of internet writing.”
Headlines and Opening Lines
In social media, you might have a 1% click-through rate on a headline. Good headline writing can push that to 10%. The difference is enormous.
Sam thinks in headlines even when not writing for clicks—it helps him frame the story. He asks: “What would the YouTube title be?”
The opening line is equally important. If the “slope isn’t slippery enough,” people won’t keep reading. It’s not that articles are too long; it’s that the opening doesn’t earn the reader’s attention.
He compares this to comedy: a great hour-long stand-up set pays off every 60–90 seconds. Same with long writing.
Boldness as a Writing Philosophy
Sam has “Bold Fast Fun” tattooed on his arm. It’s his business motto.
Boldness, for him, comes out when he’s relaxed and in flow—not when he’s at a desk in “work mode.” Copy work helps him get into that state.
He believes the best writing comes in editing: delete the first five paragraphs, then the real piece starts. As David Ogilvy said (paraphrased): “I’m a lousy writer but a world-class editor.”
For Write of Passage’s homepage, Sam’s advice: make a concrete, falsifiable promise at the top. “38 people from our last cohort called it life-changing” is a strong line—put it at the top, not buried at the bottom.
Moving Fast
Sam believes in immediate execution: if you have an idea, post it, share it, or stake money on it right away. “Put your back against the wall.”
He uses voice transcription (GPT-based, not Siri) to capture ideas the moment they happen—on walks, at dinner—so the “fire of an epiphany” never dies.
He maintains a secret blog that no one knows about, but it gets 100 visitors a day from search. Just knowing it exists makes him feel “on the hook” to keep writing.
Writing the Vision for Hampton
At The Hustle, Sam was good at writing what the company stood for but bad at writing what it stood against. He hired people who called themselves “artists” because he liked art, but they were too slow for the pace he needed.
At Hampton, he was deliberate about defining what the brand is and isn’t: it’s masculine (not in a sexist way, but in the sense of aggressive growth—business and emotional), it’s exclusive, and it’s not for everyone.
He’s inspired by the Magna Carta and the U.S. Constitution—documents where the authors chose words with extreme precision, and those words still shape society centuries later. The person who writes the rules has invisible power.
His career advice: whenever possible, be the person who writes. The writer sets the frame. The Overton window is shaped by whoever puts words on paper first.
Reading Habits
Sam reads a 300-page book in about 6–8 hours, mostly in the evening on his Kindle (history, thrillers, narrative non-fiction). During the day, he reads for enrichment (currently: a history of Berkshire Hathaway’s acquisitions, since Hampton is doing well and he’s thinking about reinvestment).
He uses Goodreads heavily—he likes it because reviewers are harsher than on Amazon, so anything above a 4.2 is world-class. He tracks books on lists and browses curated lists (e.g., “best books about the Gilded Age”).
His favorite era to read about: 1880–1920 in America—post-Civil War, pre-regulation, full of monopolies, corruption, and wild stories.
He doesn’t drink, doesn’t go to bars, exercises a lot, and reads at night. That’s his life.
Dharmesh Shah and the Elements of Eloquence
Dharmesh Shah (CTO of HubSpot, co-founder, likely a multi-billionaire) told Sam that copywriting is the most undervalued asset in business. He recommended Sam read Elements of Eloquence by Mark Forsyth—a book about rhetorical devices that make phrases memorable.
Dharmesh used it to improve his annual speech at Inbound (HubSpot’s conference). He ran an experiment: he gave the same speech to 10 groups of 10 employees, using a Zoom plugin to count laughs, then honed the material until he was getting a laugh every 90 seconds. The next year, his goal was more memorable phrases—and Elements of Eloquence helped him do it.
Sam shared several devices from the book:
Antithesis: “Ask not what your country can do for you, but what you can do for your country.” Or: “We choose to go to the moon not because it’s easy, but because it’s hard.”
Polyptoton: Using the same word twice with different meanings. “Forgive us our trespasses as we forgive those who trespass against us.”
Merism: Using words for their sound and rhythm, not just meaning. “Ladies and gentlemen” instead of “everyone.” “Hook, line, and sinker” instead of “everything.” “One small step for man, one giant leap for mankind” (the famous glitch that made it better).
Sam’s takeaway: these devices fly in the face of “remove everything unnecessary,” but they give writing soul.
Imposter Syndrome
Sam’s view: imposter syndrome never goes away. He cites a story where Neil Gaiman (the fiction writer) attended a party full of high-achievers and said, “I have such bad impostor syndrome. Everyone here has built businesses, won Olympic medals, written great books. All I did was go where I was told.” (Referring to Neil Armstrong.)
Sam has had dinner with billionaires through HustleCon and Hampton. It doesn’t go away at any level.
Sam’s Relationship with History and Motivation
He reads about cult leaders, presidents, and propagandists—not to emulate their manipulation, but to understand how repetition and memorable phrasing shape behavior.
“Repetition is indistinguishable from truth” in the human mind. Good phrases change behavior even when they’re logically wrong (e.g., “I might as well keep waiting in line” when you should just leave).
He’s driven by a need to prove himself—to a high school girlfriend who rejected him, to his father. He describes himself as “soft” and reads about people who endured extreme hardship to remind himself that his own work isn’t that hard.
